1H-INDENE-2-ACETIC ACID,2,3-DIHYDRO-,METHYL ESTER

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

实验步骤: A solution of 49.6 g (0.40 mole) dimethyl methylphosphonate (Aldrich) in 500 ml dry tetrahydrofuran is cooled to -78° in a dry nitrogen atmosphere. To the stirred phosphonate solution is added 188 ml of 2.34 M n-butyllithium in hexane solution (Alfa Inorganics, Inc.) dropwise over a period of 40 minutes at such a rate that the reaction temperature never rises above -65°. After an additional 5 minutes stirring at -78°, 36.0 g (0.20 mole) methyl (2-indanyl)acetate added dropwise at a rate that keeps the reaction temperature less than -70° (20 minutes). After 1.0 hour at -78° the reaction mixture is allowed to warm to ambient temperature, neutralized with 25 ml acetic acid and rotary evaporated to a white gel. The gelatinous material is taken up in 75 ml water, the aqueous phase extracted with 100 ml portions of choroform (3x), the combined organic extracts are backwashed (50 cc H2O), dried (MgSO4), and concentrated (water aspirator) to a crude residue and distilled, dimethyl 2-oxo-3-(2-indanyl) propylphosphonate. the reaction temperature less than -70° (20 minutes) After 1.0 hour at -78° the reaction mixture is allowed rotary evaporated to a white gel the aqueous phase extracted with 100 ml portions of choroform (3x) dried (MgSO4) concentrated (water aspirator) to a crude residue distilled

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

实验步骤: A solution of 49.6 g (0.40 mole) dimethyl methylphosphonate (Aldrich) in 500 ml dry tetrahydrofuran is cooled to -78° in a dry nitrogen atmosphere. To the stirred phosphonate solution is added 188 ml of 2.34 M n-butyllithium in hexane solution (Alfa Inorganics, Inc.) dropwise over a period of 40 minutes at such a rate that the reaction temperature never rises above -65°. After an additional 5 minutes stirring at -78°, 36.0 g (0.20 mole) methyl (2-indanyl)acetate added dropwise at a rate that keeps the reaction temperature less than -70° (20 minutes). After 1.0 hour at -78° the reaction mixture is allowed to warm to ambient temperature, neutralized with 25 ml acetic acid and rotary evaporated to a white gel. The gelatinous material is taken up in 75 ml water, the aqueous phase extracted with 100 ml portions of choroform (3x), the combined organic extracts are backwashed (50 cc H2O), dried (MgSO4), and concentrated (water aspirator) to a crude residue and distilled, dimethyl 2-oxo-3-(2-indanyl) propylphosphonate. the reaction temperature less than -70° (20 minutes) After 1.0 hour at -78° the reaction mixture is allowed rotary evaporated to a white gel the aqueous phase extracted with 100 ml portions of choroform (3x) dried (MgSO4) concentrated (water aspirator) to a crude residue distilled

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

实验步骤: A solution of 49.6 g (0.40 mole) dimethyl methylphosphonate (Aldrich) in 500 ml dry tetrahydrofuran is cooled to -78° in a dry nitrogen atmosphere. To the stirred phosphonate solution is added 188 ml of 2.34 M n-butyllithium in hexane solution (Alfa Inorganics, Inc.) dropwise over a period of 40 minutes at such a rate that the reaction temperature never rises above -65°. After an additional 5 minutes stirring at -78°, 36.0 g (0.20 mole) methyl (2-indanyl)acetate added dropwise at a rate that keeps the reaction temperature less than -70° (20 minutes). After 1.0 hour at -78° the reaction mixture is allowed to warm to ambient temperature, neutralized with 25 ml acetic acid and rotary evaporated to a white gel. The gelatinous material is taken up in 75 ml water, the aqueous phase extracted with 100 ml portions of choroform (3x), the combined organic extracts are backwashed (50 cc H2O), dried (MgSO4), and concentrated (water aspirator) to a crude residue and distilled, dimethyl 2-oxo-3-(2-indanyl) propylphosphonate. the reaction temperature less than -70° (20 minutes) After 1.0 hour at -78° the reaction mixture is allowed rotary evaporated to a white gel the aqueous phase extracted with 100 ml portions of choroform (3x) dried (MgSO4) concentrated (water aspirator) to a crude residue distilled

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

实验步骤: A solution of indan-2-yl-acetic acid (Lancaster, 20 g, 0.11 mol) in methanol (200 mL) was stirred and cooled to 0–10° C. in an ice bath and treated drop-wise with thionyl chloride (14.8 g, 0.125 mol). The mixture was stirred at RT for 16 h, concentrated in vacuo, and the oily residue was dissolved in ethyl acetate, washed with 2.5 N sodium hydroxide, water, and brine, dried (MgSO4), and concentrated in vacuo to give the title compound (21 g, 97%) which solidified. cooled to 0–10° C. in an ice bath concentrated in vacuo the oily residue was dissolved in ethyl acetate washed with 2.5 N sodium hydroxide, water, and brine dried (MgSO4) concentrated in vacuo

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

实验步骤: Under nitrogen atmosphere, 2-(2,3-dihydro-1H-inden-2-yl)acetic acid (Lanc, 19.6 g, 111 mmol) was dissolved in methanol (100 mL) and cooled in an ice bath. Thionyl chloride (9.7 mL, 133 mmol) was slowly added dropwise thereto under stirring. After completing the dropwise addition, the ice bath was removed and the reaction solution was additionally stirred for 30 minutes. Upon the completion of the reaction, the reaction solution was added in small portions to ice-cold sodium bicarbonate solution under stirring. The reaction mixture was extracted twice with ethyl acetate, and the obtained organic layer was washed once with water, dried over anhydrous magnesium sulfate, and the reaction solution was concentrated to obtain the target compound (21.2 g, Yield 100%). cooled in an ice bath the dropwise addition the ice bath was removed the reaction solution was additionally stirred for 30 minutes Upon the completion of the reaction the reaction solution was added in small portions to ice-cold sodium bicarbonate solution under stirring The reaction mixture was extracted twice with ethyl acetate the obtained organic layer was washed once with water dried over anhydrous magnesium sulfate the reaction solution was concentrated

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

实验步骤: 160 ml of methylene chloride was added with 52.9 g (0.388 mol) of anhydrous aluminum chloride, and further added with 40 ml of methylene chloride containing 25.03 g (0.132 mol) of methyl(indan-2-yl)acetate under ice-cooling. Subsequently, 13.1 ml (0.185 mol) of acetyl chloride was added thereto dropwise. Stirring was conducted for 40 minutes at the same temperature. The reaction mixture was poured into ice-water and the organic phase was collected. After washing and drying, the solvent was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 27.8 g of an oily product. Yield: 91% cooling the organic phase was collected After washing drying condensed under reduced pressure the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

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

实验步骤: 1.02 g (26.8 mmol) of lithium aluminum hydride was suspended in 100 ml of tetrahydrofuran, to which was added dropwise a solution of 10 ml tetrafuran containing 5.06 g (26.6 mmol) of methyl(indan-2-yl)acetate under ice-cooling. After completion of the addition, stirring was continued for 1 hour, during which 1 ml water, 1 ml of 15% sodium hydroxide and 3 ml water were added dropwise in this order for decomposing the excessive reducing agent. The solid matter was removed by filtration, the filtrate was condensed and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 4.30 g of a colorless oil. Yield: 100% cooling After completion of the addition were added dropwise in this order The solid matter was removed by filtration condensed the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

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

实验步骤: Added to 160 ml of methylene chloride were 52.9 g (0.388 mol) of anhydrous aluminum chloride. While chilling with ice water, a solution of 25.03 g (0.132 mol) of methyl (indan-2-yl)acetate in 40 ml of methylene chloride was added dropwise to the solution, followed by the addition of 13.1 ml (0.185 mol) of acetyl chloride. After stirring the mixture at the same temperature for 40 minutes, the reaction mixture was poured into ice water to take out an organic layer separated. After the organic layer was washed with water and dried, the solvent was distilled off under reduced pressure. The resultant residue was purified by column chromatography on silica gel (ethyl acetate-hexane=1:2), thereby obtaining 27.8 g of an oily substance. Yield: 91%. separated After the organic layer was washed with water dried the solvent was distilled off under reduced pressure The resultant residue was purified by column chromatography on silica gel (ethyl acetate-hexane=1:2) obtaining 27.8 g of an oily substance

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

实验步骤: Suspended in 100 ml of tetrahydrofuran were 1.02 g (26.8 mmol) of lithium aluminum hydride, and a solution of 5.06 g (26.6 mmol) of methyl (indan-2-yl)acetate in 10 ml of tetrahydrofuran was added dropwise to the suspension while chilling with ice water. After the addition, the mixture was stirred for 1 hour, and 1 ml of water, 1 ml of 15% sodium hydroxide and 3 ml of water were successively added dropwise to the mixture to decompose excess of the reducing agent. Solids were separated by filtration, the filtrate was concentrated, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4), thereby obtaining 4.30 g of a colorless oily substance. Yield: 100%. After the addition Solids were separated by filtration the filtrate was concentrated the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) obtaining 4.30 g of a colorless oily substance

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

实验步骤: A solution of 49.6 g (0.40 mole) dimethyl methylphosphonate (Aldrich) in 500 ml dry tetrahydrofuran is cooled to -78° in a dry nitrogen atmosphere. To the stirred phosphonate solution is added 188 ml of 2.34 M n-butyllithium in hexane solution (Alfa Inorganics, Inc.) dropwise over a period of 40 minutes at such a rate that the reaction temperature never rises above -65°. After an additional 5 minutes stirring at -78°, 36.0 g (0.20 mole) methyl (2-indanyl)acetate added dropwise at a rate that keeps the reaction temperature less than -70° (20 minutes). After 1.0 hour at -78° the reaction mixture is allowed to warm to ambient temperature, neutralized with 25 ml acetic acid and rotary evaporated to a white gel. The gelatinous material is taken up in 75 ml water, the aqueous phase extracted with 100 ml portions of choroform (3x), the combined organic extracts are backwashed (50 cc H2O), dried (MgSO4), and concentrated (water aspirator) to a crude residue and distilled, dimethyl 2-oxo-3-(2-indanyl) propylphosphonate. the reaction temperature less than -70° (20 minutes) After 1.0 hour at -78° the reaction mixture is allowed rotary evaporated to a white gel the aqueous phase extracted with 100 ml portions of choroform (3x) dried (MgSO4) concentrated (water aspirator) to a crude residue distilled