10-溴代癸酸乙酯

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4.4 g (0.018 mole) of 10-bromodecanoic acid, 3 ml of methane sulfonic acid, and 250 ml of absolute ethanol was heated at reflux for 2 h. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to yield 5.0 g (100%) of ethyl 10-bromodecanoate as a yellow oil. A mixture of 4.6 g (0.015 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.2 g (0.015 mole) of ethyl 10-bromodecanoate, 6.4 g (0.015 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 ml of N,N-dimethylformamide was heated on a steam bath fo 6 h. The mixture was poured into 1 L of water and extracted three times with 250 ml portions of ethyl acetate. The ethyl acetate extracts were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a dark oil. The oil was purified by high pressure liquid chromatography (Water Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min). The fractions containing the desired product were combined and concentrated under reduced pressure to yield 4.5 g (60%) of the title compound as a golden, viscous oil. was heated on a steam bath extracted three times with 250 ml portions of ethyl acetate washed with water and brine dried (MgSO4) concentrated under reduced pressure to give a dark oil The oil was purified by high pressure liquid chromatography (Water Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min) The fractions containing the desired product concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4.4 g (0.018 mole) of 10-bromodecanoic acid, 3 ml of methane sulfonic acid, and 250 ml of absolute ethanol was heated at reflux for 2 h. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to yield 5.0 g (100%) of ethyl 10-bromodecanoate as a yellow oil. A mixture of 4.6 g (0.015 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.2 g (0.015 mole) of ethyl 10-bromodecanoate, 6.4 g (0.015 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 ml of N,N-dimethylformamide was heated on a steam bath fo 6 h. The mixture was poured into 1 L of water and extracted three times with 250 ml portions of ethyl acetate. The ethyl acetate extracts were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a dark oil. The oil was purified by high pressure liquid chromatography (Water Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min). The fractions containing the desired product were combined and concentrated under reduced pressure to yield 4.5 g (60%) of the title compound as a golden, viscous oil. at reflux for 2 h The mixture was concentrated under reduced pressure the residue partitioned between ethyl acetate and water The organic layer was washed with water and brine dried (MgSO4) concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To this end, the 180.5 g of 10-bromodecanoic acid from Step II was added to the 11 reactor (described above) along with 645 g of absolute ethanol. The mixture was heated and stirred for about 3.5 h. GC analysis confirmed that reaction was completed when 10-bromodecanoic acid could not be detected. Next, excess ethanol and residual water were removed through evaporation leaving 197.8 g of 94.9% pure ethyl 10-bromodecanoate residue. 150 g MTBE was added to the ethyl 10-bromodecanoate residue which then was washed repeatedly with 10% sodium carbonate solution followed by water. The mixture was phase separated to obtain 340.7 g of a mixture of ethyl 10-bromodecanoate and MTBE. According to GC analysis the yield from Steps II and III was 89.7%. The mixture was heated GC analysis confirmed that reaction Next, excess ethanol and residual water were removed through evaporation

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To this end, the 180.5 g of 10-bromodecanoic acid from Step II was added to the 11 reactor (described above) along with 645 g of absolute ethanol. The mixture was heated and stirred for about 3.5 h. GC analysis confirmed that reaction was completed when 10-bromodecanoic acid could not be detected. Next, excess ethanol and residual water were removed through evaporation leaving 197.8 g of 94.9% pure ethyl 10-bromodecanoate residue. 150 g MTBE was added to the ethyl 10-bromodecanoate residue which then was washed repeatedly with 10% sodium carbonate solution followed by water. The mixture was phase separated to obtain 340.7 g of a mixture of ethyl 10-bromodecanoate and MTBE. According to GC analysis the yield from Steps II and III was 89.7%. The mixture was heated GC analysis confirmed that reaction Next, excess ethanol and residual water were removed through evaporation

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The order of functionalization and esterification is not critical. For example, rather than performing an ozonolysis of the starting material, for example, 10-undecylenic acid, as described above, the starting material first may be esterified with ethanol or other alcohol to form an ester, for example, ethyl 10-undecylenate. Next, the ester can undergo functionalization by first ozonating the ester and then reducing the ozonide using, for example, sodium borohydride to form a hydroxylated ester, for example, ethyl 10-hydroxydecanoate. The hydroxylated ester finally is converted to the desired functionalized ester using, for example, PBr3 to form ethyl 10-bromodecanoate.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4.4 g (0.018 mole) of 10-bromodecanoic acid, 3 ml of methane sulfonic acid, and 250 ml of absolute ethanol was heated at reflux for 2 h. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to yield 5.0 g (100%) of ethyl 10-bromodecanoate as a yellow oil. A mixture of 4.6 g (0.015 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.2 g (0.015 mole) of ethyl 10-bromodecanoate, 6.4 g (0.015 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 ml of N,N-dimethylformamide was heated on a steam bath fo 6 h. The mixture was poured into 1 L of water and extracted three times with 250 ml portions of ethyl acetate. The ethyl acetate extracts were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a dark oil. The oil was purified by high pressure liquid chromatography (Water Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min). The fractions containing the desired product were combined and concentrated under reduced pressure to yield 4.5 g (60%) of the title compound as a golden, viscous oil. was heated on a steam bath extracted three times with 250 ml portions of ethyl acetate washed with water and brine dried (MgSO4) concentrated under reduced pressure to give a dark oil The oil was purified by high pressure liquid chromatography (Water Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min) The fractions containing the desired product concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4.4 g (0.018 mole) of 10-bromodecanoic acid, 3 ml of methane sulfonic acid, and 250 ml of absolute ethanol was heated at reflux for 2 h. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to yield 5.0 g (100%) of ethyl 10-bromodecanoate as a yellow oil. A mixture of 4.6 g (0.015 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.2 g (0.015 mole) of ethyl 10-bromodecanoate, 6.4 g (0.015 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 ml of N,N-dimethylformamide was heated on a steam bath fo 6 h. The mixture was poured into 1 L of water and extracted three times with 250 ml portions of ethyl acetate. The ethyl acetate extracts were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a dark oil. The oil was purified by high pressure liquid chromatography (Water Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min). The fractions containing the desired product were combined and concentrated under reduced pressure to yield 4.5 g (60%) of the title compound as a golden, viscous oil. at reflux for 2 h The mixture was concentrated under reduced pressure the residue partitioned between ethyl acetate and water The organic layer was washed with water and brine dried (MgSO4) concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To this end, the 180.5 g of 10-bromodecanoic acid from Step II was added to the 11 reactor (described above) along with 645 g of absolute ethanol. The mixture was heated and stirred for about 3.5 h. GC analysis confirmed that reaction was completed when 10-bromodecanoic acid could not be detected. Next, excess ethanol and residual water were removed through evaporation leaving 197.8 g of 94.9% pure ethyl 10-bromodecanoate residue. 150 g MTBE was added to the ethyl 10-bromodecanoate residue which then was washed repeatedly with 10% sodium carbonate solution followed by water. The mixture was phase separated to obtain 340.7 g of a mixture of ethyl 10-bromodecanoate and MTBE. According to GC analysis the yield from Steps II and III was 89.7%. The mixture was heated GC analysis confirmed that reaction Next, excess ethanol and residual water were removed through evaporation

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The order of functionalization and esterification is not critical. For example, rather than performing an ozonolysis of the starting material, for example, 10-undecylenic acid, as described above, the starting material first may be esterified with ethanol or other alcohol to form an ester, for example, ethyl 10-undecylenate. Next, the ester can undergo functionalization by first ozonating the ester and then reducing the ozonide using, for example, sodium borohydride to form a hydroxylated ester, for example, ethyl 10-hydroxydecanoate. The hydroxylated ester finally is converted to the desired functionalized ester using, for example, PBr3 to form ethyl 10-bromodecanoate.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4.4 g (0.018 mole) of 10-bromodecanoic acid, 3 ml of methane sulfonic acid, and 250 ml of absolute ethanol was heated at reflux for 2 h. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to yield 5.0 g (100%) of ethyl 10-bromodecanoate as a yellow oil. A mixture of 4.6 g (0.015 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.2 g (0.015 mole) of ethyl 10-bromodecanoate, 6.4 g (0.015 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 ml of N,N-dimethylformamide was heated on a steam bath fo 6 h. The mixture was poured into 1 L of water and extracted three times with 250 ml portions of ethyl acetate. The ethyl acetate extracts were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a dark oil. The oil was purified by high pressure liquid chromatography (Water Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min). The fractions containing the desired product were combined and concentrated under reduced pressure to yield 4.5 g (60%) of the title compound as a golden, viscous oil. was heated on a steam bath extracted three times with 250 ml portions of ethyl acetate washed with water and brine dried (MgSO4) concentrated under reduced pressure to give a dark oil The oil was purified by high pressure liquid chromatography (Water Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min) The fractions containing the desired product concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4.4 g (0.018 mole) of 10-bromodecanoic acid, 3 ml of methane sulfonic acid, and 250 ml of absolute ethanol was heated at reflux for 2 h. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to yield 5.0 g (100%) of ethyl 10-bromodecanoate as a yellow oil. A mixture of 4.6 g (0.015 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.2 g (0.015 mole) of ethyl 10-bromodecanoate, 6.4 g (0.015 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 ml of N,N-dimethylformamide was heated on a steam bath fo 6 h. The mixture was poured into 1 L of water and extracted three times with 250 ml portions of ethyl acetate. The ethyl acetate extracts were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a dark oil. The oil was purified by high pressure liquid chromatography (Water Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min). The fractions containing the desired product were combined and concentrated under reduced pressure to yield 4.5 g (60%) of the title compound as a golden, viscous oil. at reflux for 2 h The mixture was concentrated under reduced pressure the residue partitioned between ethyl acetate and water The organic layer was washed with water and brine dried (MgSO4) concentrated under reduced pressure