Reacción #49705

Ecuación de reacción

4-benzyloxybenzoic acid chloride

(R)-(+)-1,1,1-trifluoro-2-octanol

dimethylaminopyridine

triethylamine

→

titled compound

Rendimiento 61.2%

(R)-(+)-1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate

Rendimiento 61.2%

Disolventes

—

ice water

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.WAITThe mixture was left
3. 3
   OtroThe methylene chloride layer separated
4. 4
   Lavadowas washed with diluted hydrochloric acid, water, 1N aqueous sodium carbonate solution and water in this order
5. 5
   Secadobefore being dried over magnesium sulfate
6. 6
   workup.DISTILLATIONAfter distillation
7. 7
   Otrowas over purification by toluene/silica gel chromatography and recrystallization from ethanol

Procedimiento

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).

Fuente