(2R)-1,1,1-trifluorooctan-2-ol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxybiphenyl-4'-carboxylic acid chloride (1.23 g) in methylene chloride (10 ml) was added by little and little under ice-cooling a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (0.96 g) ([α]D22.5 =+20.1, optical purity 96.3%ee), dimethyl-aminopyridine (0.55 g) and triethylamine (0.48 g) in methylene chloride (20 ml). The mixture was left to stand over-night at room temperature in order to complete the reaction before the mixture obtained was poured in ice-water. The mixture was left to stand over-night at room temperature in order the reaction before the mixture obtained

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxybiphenyl-4'-carboxylic acid chloride (1.23 g) in methylene chloride (10 ml) was added by little and little under ice-cooling a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (0.96 g) ([α]D22.5 =+20.1, optical purity 96.3%ee), dimethyl-aminopyridine (0.55 g) and triethylamine (0.48 g) in methylene chloride (20 ml). The mixture was left to stand over-night at room temperature in order to complete the reaction before the mixture obtained was poured in ice-water. The mixture was left to stand over-night at room temperature in order the reaction before the mixture obtained

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into methylene chloride (20 ml) were added 4,4'-biphenyldicarboxylic acid chloride (0.5 g), (R)-(+)-1,1,1-trifluoro-2-octanol (0.15 g), triethylamine (0.09 g) and dimethylaminopyridine (0.03 g) and the mixture was left to stand for 8 hours in order to allow a reaction to proceed. Thereto were added 2-fluoro-4-decyloxyphenol (0.22 g) and triethylamine (0.09 g), and the mixture was left to stand for 8 hours in order to allow a reaction to proceed. The product was made acidic with 1N hydrochloric acid and extracted with methylene chloride. The extracted layer was washed with 1N aqueous sodium carbonate solution, water, aqueous sodium chloride solution (saturated) and water, in this order, until it was neutralized. After the product was dried over anhydrous magnesium sulfate, it was distilled under reduced pressure to remove the solvent. A solid product thus obtained was purified by silica-gel column chromatography until the titled compound (0.48 g) was obtained. the mixture was left a reaction the mixture was left to stand for 8 hours in order a reaction extracted with methylene chloride The extracted layer was washed with 1N aqueous sodium carbonate solution, water, aqueous sodium chloride solution (saturated) and water, in this order, until it After the product was dried over anhydrous magnesium sulfate, it was distilled under reduced pressure to remove the solvent A solid product thus obtained was purified by silica-gel column chromatography until the titled compound (0.48 g) was obtained

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into methylene chloride (20 ml) were added 4,4'-biphenyldicarboxylic acid chloride (0.5 g), (R)-(+)-1,1,1-trifluoro-2-octanol (0.15 g), triethylamine (0.09 g) and dimethylaminopyridine (0.03 g) and the mixture was left to stand for 8 hours in order to allow a reaction to proceed. Thereto were added 2-fluoro-4-decyloxyphenol (0.22 g) and triethylamine (0.09 g), and the mixture was left to stand for 8 hours in order to allow a reaction to proceed. The product was made acidic with 1N hydrochloric acid and extracted with methylene chloride. The extracted layer was washed with 1N aqueous sodium carbonate solution, water, aqueous sodium chloride solution (saturated) and water, in this order, until it was neutralized. After the product was dried over anhydrous magnesium sulfate, it was distilled under reduced pressure to remove the solvent. A solid product thus obtained was purified by silica-gel column chromatography until the titled compound (0.48 g) was obtained. the mixture was left a reaction the mixture was left to stand for 8 hours in order a reaction extracted with methylene chloride The extracted layer was washed with 1N aqueous sodium carbonate solution, water, aqueous sodium chloride solution (saturated) and water, in this order, until it After the product was dried over anhydrous magnesium sulfate, it was distilled under reduced pressure to remove the solvent A solid product thus obtained was purified by silica-gel column chromatography until the titled compound (0.48 g) was obtained

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxybiphenyl-4'-carboxylic acid chloride (1.23 g) in methylene chloride (10 ml) was added by little and little under ice-cooling a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (0.96 g) ([α]D22.5 =+20.1, optical purity 96.3%ee), dimethyl-aminopyridine (0.55 g) and triethylamine (0.48 g) in methylene chloride (20 ml). The mixture was left to stand over-night at room temperature in order to complete the reaction before the mixture obtained was poured in ice-water. The mixture was left to stand over-night at room temperature in order the reaction before the mixture obtained

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into methylene chloride (20 ml) were added 4,4'-biphenyldicarboxylic acid chloride (0.5 g), (R)-(+)-1,1,1-trifluoro-2-octanol (0.15 g), triethylamine (0.09 g) and dimethylaminopyridine (0.03 g) and the mixture was left to stand for 8 hours in order to allow a reaction to proceed. Thereto were added 2-fluoro-4-decyloxyphenol (0.22 g) and triethylamine (0.09 g), and the mixture was left to stand for 8 hours in order to allow a reaction to proceed. The product was made acidic with 1N hydrochloric acid and extracted with methylene chloride. The extracted layer was washed with 1N aqueous sodium carbonate solution, water, aqueous sodium chloride solution (saturated) and water, in this order, until it was neutralized. After the product was dried over anhydrous magnesium sulfate, it was distilled under reduced pressure to remove the solvent. A solid product thus obtained was purified by silica-gel column chromatography until the titled compound (0.48 g) was obtained. the mixture was left a reaction the mixture was left to stand for 8 hours in order a reaction extracted with methylene chloride The extracted layer was washed with 1N aqueous sodium carbonate solution, water, aqueous sodium chloride solution (saturated) and water, in this order, until it After the product was dried over anhydrous magnesium sulfate, it was distilled under reduced pressure to remove the solvent A solid product thus obtained was purified by silica-gel column chromatography until the titled compound (0.48 g) was obtained

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxybenzoic acid chloride (4.3 g) in methylene chloride (50 ml) was added a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (2.9 g) ([α]D22.5 =+20.1, optical purity 96.3 % ee), dimethylaminopyridine (0.6 g) and triethylamine (1.7 g) in methylene chloride (50 ml) under ice-cooling. The mixture was left to stand at the room temperature for 24 hours before being poured in ice water. The methylene chloride layer separated was washed with diluted hydrochloric acid, water, 1N aqueous sodium carbonate solution and water in this order before being dried over magnesium sulfate. After distillation was over purification by toluene/silica gel chromatography and recrystallization from ethanol gave the titled compound (3.8 g). cooling The mixture was left The methylene chloride layer separated was washed with diluted hydrochloric acid, water, 1N aqueous sodium carbonate solution and water in this order before being dried over magnesium sulfate After distillation was over purification by toluene/silica gel chromatography and recrystallization from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxybenzoic acid chloride (4.3 g) in methylene chloride (50 ml) was added drop by drop a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (2.9 g), dimethylaminopyridine (0.6 g) and triethylamine (1.7 g) in methylene chloride (50 ml), under ice cooling. The mixture was left to stand at the room temperature for 24 hours before being poured in ice water. The methylene chloride layer separated was washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order, dried over magnesium sulfate and distilled to obtain a crude objective compound. The compound was purified by toluene/silica gel chromatography and recrystallization from ethanol to obtain the titled compound (3.8 g). The mixture was left The methylene chloride layer separated was washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order dried over magnesium sulfate distilled to obtain a crude objective compound The compound was purified by toluene/silica gel chromatography and recrystallization from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of 0.37 g (1.1 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid (R)-1-methylheptyl ester obtained as in the fourth stage of Example 23 where (R)-1-methyl heputanol was used in stead of (R)-1-trifluoromethylheptanol, 0.33 g (1.1 mmol) of 4'-decylbiphenyl-4-carboxylic acid (FK-1124-10 from Teikoku Kagaku Sangyo K.K.), 0.013 g (0.11 mmol) of 4-N,N-dimethylaminopyridine and 10 ml of methylene chloride was added dropwise 5 ml of a methylene chloride solution containing 0.27 g (1.3 mmol) of N,N'-dicyclohexylcarbodiimide with stirring at room temperature over a period of 2.5 hours. obtained as in the fourth stage of Example 23 where (R)-1-methyl heputanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of 0.31 g (1 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid (R)-1-methylheptyl ester obtained as in the fourth stage of Example 23 where R-1-methyl heputanol was used in stead of (R)-1-trifluoromethylheptanol, 0.31 g (1 mmol) of 4'-octylbiphenyl-4-carboxylic acid (FK-1124-8 from Teikoku Kagaku Sangyo K.K.), 0.02 g (0.16 mmol) of 4-N,N-dimethylaminopyridine and 15 ml of methylene chloride was added dropwise 3 ml of a methylene chloride solution containing 0.27 g (1.3 mmol) of N,N'-dicyclohexylcarbodiimide with stirring at room temperature over a period of 3 hours. obtained as in the fourth stage of Example 23 where R-1-methyl heputanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxybenzoic acid chloride (4.3 g) in methylene chloride (50 ml) was added a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (2.9 g) ([α]D22.5 =+20.1, optical purity 96.3 % ee), dimethylaminopyridine (0.6 g) and triethylamine (1.7 g) in methylene chloride (50 ml) under ice-cooling. The mixture was left to stand at the room temperature for 24 hours before being poured in ice water. The methylene chloride layer separated was washed with diluted hydrochloric acid, water, 1N aqueous sodium carbonate solution and water in this order before being dried over magnesium sulfate. After distillation was over purification by toluene/silica gel chromatography and recrystallization from ethanol gave the titled compound (3.8 g). cooling The mixture was left The methylene chloride layer separated was washed with diluted hydrochloric acid, water, 1N aqueous sodium carbonate solution and water in this order before being dried over magnesium sulfate After distillation was over purification by toluene/silica gel chromatography and recrystallization from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxybenzoic acid chloride (4.3 g) in methylene chloride (50 ml) was added drop by drop a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (2.9 g), dimethylaminopyridine (0.6 g) and triethylamine (1.7 g) in methylene chloride (50 ml), under ice cooling. The mixture was left to stand at the room temperature for 24 hours before being poured in ice water. The methylene chloride layer separated was washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order, dried over magnesium sulfate and distilled to obtain a crude objective compound. The compound was purified by toluene/silica gel chromatography and recrystallization from ethanol to obtain the titled compound (3.8 g). The mixture was left The methylene chloride layer separated was washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order dried over magnesium sulfate distilled to obtain a crude objective compound The compound was purified by toluene/silica gel chromatography and recrystallization from ethanol