Reaktion #49705

Reaktionsgleichung

4-benzyloxybenzoic acid chloride

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

dimethylaminopyridine

triethylamine

→

titled compound

Ausbeute 61.2%

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

Ausbeute 61.2%

Lösungsmittel

—

ice water

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle