甲基3-氧代十八酸乙酯

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: Into a 200-ml autoclave (made of Hastelloy) were introduced 50 g of the methyl 3-oxooctadecanoate obtained above and 50 ml of methanol. The atmosphere in the autoclave was replaced with nitrogen gas. Thereto was added a solution prepared by dissolving 325 mg of Ru2Cl4 ((+)-(T)BINAP)2Et3N as a ruthenium-optically active phosphine complex in 3.8 ml of methylene chloride. Asymmetric hydrogenation was conducted at 65° C. and a hydrogen pressure of 30 atm. After the reaction mixture was thus reacted for 12 hours, it was taken out of the autoclave. The reaction product was recrystallized from methanol to obtain 47.8 g of methyl (R)-3-hydroxyoctadecanoate. Yield, 95%. Thereto was added a solution prepared was conducted at 65° C. After the reaction mixture was thus reacted for 12 hours The reaction product was recrystallized from methanol

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

实验步骤: Into a 200-ml autoclave (made of Hastelloy) were introduced 50 g of the methyl 3-oxooctadecanoate obtained above and 50 ml of methanol. The atmosphere in the autoclave was replaced with nitrogen gas. Thereto was added a solution prepared by dissolving 325 mg of Ru2Cl4 ((+)-(T)BINAP)2Et3N as a ruthenium-optically active phosphine complex in 3.8 ml of methylene chloride. Asymmetric hydrogenation was conducted at 65° C. and a hydrogen pressure of 30 atm. After the reaction mixture was thus reacted for 12 hours, it was taken out of the autoclave. The reaction product was recrystallized from methanol to obtain 47.8 g of methyl (R)-3-hydroxyoctadecanoate. Yield, 95%. Thereto was added a solution prepared was conducted at 65° C. After the reaction mixture was thus reacted for 12 hours The reaction product was recrystallized from methanol

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

实验步骤: Four liters of a suspension of 440 g (11 mol) of 60% sodium hydride in dried tetrahydrofuran was cooled to 0° C. Thereto was added dropwise 1.8 L of a tetrahydrofuran solution of 1.161 kg (10 mol) of methyl acetoacetate. After this mixture was stirred at room temperature for 1 hour, 3.023 kg (11 mol) of hexadecanoyl chloride was added dropwise at 0 to 5° C. and the resultant mixture was stirred at room temperature overnight. Thereafter, the tetrahydrofuran was distilled off, and the residue was poured into ice water and extracted with 8 L of ethyl acetate. The ethyl acetate was distilled off, and the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 L of methanol. The resultant mixture was stirred with heating at 60 to 65° C. for 6 hours. The reaction mixture was cooled with ice, and the pH thereof was then adjusted to 5 with 10% sulfuric acid. This reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with 5% aqueous sodium carbonate solution and saturated aqueous common salt solution. Thereafter, the ethyl acetate was distilled off and the concentrate was recrystallized from methanol to obtain 1.72 kg (5.5 mol) of methyl 3-oxooctadecanoate. Yield, 55%. Thereafter, the tetrahydrofuran was distilled off the residue was poured into ice water extracted with 8 L of ethyl acetate The ethyl acetate was distilled off the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 L of methanol The resultant mixture was stirred with heating at 60 to 65° C. for 6 hours The reaction mixture was cooled with ice This reaction mixture was extracted with ethyl acetate The ethyl acetate layer was washed with 5% aqueous sodium carbonate solution and saturated aqueous common salt solution Thereafter, the ethyl acetate was distilled off the concentrate was recrystallized from methanol

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

实验步骤: A dry tetrahydrofuran suspension (2 l) of 228 g (5.7 mol) of 60% sodium hydride was cooled to 0° C., and 1.8 l of a tetrahydrofuran solution of 638 g (5.5 mol) of methyl acetoacetate was added thereto dropwise, followed by stirring at room temperature for 1 hour. To the mixture was added dropwise 1.511 kg (5.5 mol) of palmitoyl chloride at 0 to 5° C. followed by stirring at room temperature overnight. After confirming disappearance of palmitoyl chloride by TLC, tetrahydrofuran was evaporated, and the residue was poured into ice-water and extracted with 2 l of ethyl acetate. Ethyl acetate was evaporated, and the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 l of methanol. The mixture was heated at 60 to 65° C. for 6 hours while stirring to conduct deacylation. The product was cooled with ice, adjusted to pH 5 with a 10% sulfuric acid aqueous solution, and extracted with ethyl acetate. The ethyl acetate layer was washed successively with a 5% sodium carbonate aqueous solution and a saturated sodium chloride aqueous solution. Ethyl acetate was removed by evaporation, and the resulting crude crystals were recrystallized from methanol to give 858 g (2.75 mol; yield: 50.0%) of methyl 3-oxooctadecanoate (melting point: 45° C.). by stirring at room temperature overnight was evaporated the residue was poured into ice-water extracted with 2 l of ethyl acetate Ethyl acetate was evaporated the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 l of methanol The mixture was heated at 60 to 65° C. for 6 hours while stirring The product was cooled with ice extracted with ethyl acetate The ethyl acetate layer was washed successively with a 5% sodium carbonate aqueous solution Ethyl acetate was removed by evaporation the resulting crude crystals were recrystallized from methanol

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

实验步骤: A dry tetrahydrofuran suspension (2 l) of 228 g (5.7 mol) of 60% sodium hydride was cooled to 0° C., and 1.8 l of a tetrahydrofuran solution of 638 g (5.5 mol) of methyl acetoacetate was added thereto dropwise, followed by stirring at room temperature for 1 hour. To the mixture was added dropwise 1.511 kg (5.5 mol) of palmitoyl chloride at 0 to 5° C. followed by stirring at room temperature overnight. After confirming disappearance of palmitoyl chloride by TLC, tetrahydrofuran was evaporated, and the residue was poured into ice-water and extracted with 2 l of ethyl acetate. Ethyl acetate was evaporated, and the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 l of methanol. The mixture was heated at 60 to 65° C. for 6 hours while stirring to conduct deacylation. The product was cooled with ice, adjusted to pH 5 with a 10% sulfuric acid aqueous solution, and extracted with ethyl acetate. The ethyl acetate layer was washed successively with a 5% sodium carbonate aqueous solution and a saturated sodium chloride aqueous solution. Ethyl acetate was removed by evaporation, and the resulting crude crystals were recrystallized from methanol to give 858 g (2.75 mol; yield: 50.0%) of methyl 3-oxooctadecanoate (melting point: 45° C.). by stirring at room temperature overnight was evaporated the residue was poured into ice-water extracted with 2 l of ethyl acetate Ethyl acetate was evaporated the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 l of methanol The mixture was heated at 60 to 65° C. for 6 hours while stirring The product was cooled with ice extracted with ethyl acetate The ethyl acetate layer was washed successively with a 5% sodium carbonate aqueous solution Ethyl acetate was removed by evaporation the resulting crude crystals were recrystallized from methanol

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

实验步骤: Into a 200-ml autoclave (made of Hastelloy) were introduced 50 g of the methyl 3-oxooctadecanoate obtained above and 50 ml of methanol. The atmosphere in the autoclave was replaced with nitrogen gas. Thereto was added a solution prepared by dissolving 325 mg of Ru2Cl4 ((+)-(T)BINAP)2Et3N as a ruthenium-optically active phosphine complex in 3.8 ml of methylene chloride. Asymmetric hydrogenation was conducted at 65° C. and a hydrogen pressure of 30 atm. After the reaction mixture was thus reacted for 12 hours, it was taken out of the autoclave. The reaction product was recrystallized from methanol to obtain 47.8 g of methyl (R)-3-hydroxyoctadecanoate. Yield, 95%. Thereto was added a solution prepared was conducted at 65° C. After the reaction mixture was thus reacted for 12 hours The reaction product was recrystallized from methanol

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

实验步骤: Four liters of a suspension of 440 g (11 mol) of 60% sodium hydride in dried tetrahydrofuran was cooled to 0° C. Thereto was added dropwise 1.8 L of a tetrahydrofuran solution of 1.161 kg (10 mol) of methyl acetoacetate. After this mixture was stirred at room temperature for 1 hour, 3.023 kg (11 mol) of hexadecanoyl chloride was added dropwise at 0 to 5° C. and the resultant mixture was stirred at room temperature overnight. Thereafter, the tetrahydrofuran was distilled off, and the residue was poured into ice water and extracted with 8 L of ethyl acetate. The ethyl acetate was distilled off, and the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 L of methanol. The resultant mixture was stirred with heating at 60 to 65° C. for 6 hours. The reaction mixture was cooled with ice, and the pH thereof was then adjusted to 5 with 10% sulfuric acid. This reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with 5% aqueous sodium carbonate solution and saturated aqueous common salt solution. Thereafter, the ethyl acetate was distilled off and the concentrate was recrystallized from methanol to obtain 1.72 kg (5.5 mol) of methyl 3-oxooctadecanoate. Yield, 55%. Thereafter, the tetrahydrofuran was distilled off the residue was poured into ice water extracted with 8 L of ethyl acetate The ethyl acetate was distilled off the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 L of methanol The resultant mixture was stirred with heating at 60 to 65° C. for 6 hours The reaction mixture was cooled with ice This reaction mixture was extracted with ethyl acetate The ethyl acetate layer was washed with 5% aqueous sodium carbonate solution and saturated aqueous common salt solution Thereafter, the ethyl acetate was distilled off the concentrate was recrystallized from methanol

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

实验步骤: A dry tetrahydrofuran suspension (2 l) of 228 g (5.7 mol) of 60% sodium hydride was cooled to 0° C., and 1.8 l of a tetrahydrofuran solution of 638 g (5.5 mol) of methyl acetoacetate was added thereto dropwise, followed by stirring at room temperature for 1 hour. To the mixture was added dropwise 1.511 kg (5.5 mol) of palmitoyl chloride at 0 to 5° C. followed by stirring at room temperature overnight. After confirming disappearance of palmitoyl chloride by TLC, tetrahydrofuran was evaporated, and the residue was poured into ice-water and extracted with 2 l of ethyl acetate. Ethyl acetate was evaporated, and the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 l of methanol. The mixture was heated at 60 to 65° C. for 6 hours while stirring to conduct deacylation. The product was cooled with ice, adjusted to pH 5 with a 10% sulfuric acid aqueous solution, and extracted with ethyl acetate. The ethyl acetate layer was washed successively with a 5% sodium carbonate aqueous solution and a saturated sodium chloride aqueous solution. Ethyl acetate was removed by evaporation, and the resulting crude crystals were recrystallized from methanol to give 858 g (2.75 mol; yield: 50.0%) of methyl 3-oxooctadecanoate (melting point: 45° C.). by stirring at room temperature overnight was evaporated the residue was poured into ice-water extracted with 2 l of ethyl acetate Ethyl acetate was evaporated the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 l of methanol The mixture was heated at 60 to 65° C. for 6 hours while stirring The product was cooled with ice extracted with ethyl acetate The ethyl acetate layer was washed successively with a 5% sodium carbonate aqueous solution Ethyl acetate was removed by evaporation the resulting crude crystals were recrystallized from methanol