Reacción #1589080

Ecuación de reacción

(R)-(+)-3-benzyloxy-1,2-propanediol

triphenylchloromethane

THF

acetonitrile

→

1-trityl-3-benzyl-sn-glycerol

Rendimiento 94.4%

Disolventes

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was refluxed for 17 hours
2. 2
   workup.ADDITIONpoured on ice (100 grams)
3. 3
   Otrotransferred to a separatory funnel
4. 4
   Extracciónextracted thrice with 100 ml diethyl ether
5. 5
   LavadoThe organic phase was washed consecutively with 100 ml water, twice with 100 ml
6. 6
   workup.ADDITIONdilute (1.5%) sulfuric acid, 100 ml water, 100 ml concentrated sodium bicarbonate solution
7. 7
   SecadoThe organic phase was dried over anhydrous sodium sulfate
8. 8
   Otrothe solvent was removed under reduced pressure

Procedimiento

5 grams (27.44 mmol) of (R)-(+)-3-benzyloxy-1,2-propanediol and 10 grams (35.87 mmol) of triphenylchloromethane were added to 100 ml dry THF and 25 ml dry acetonitrile. 8 ml of dry triethylamine were added and the reaction mixture was refluxed for 17 hours. The reaction mixture was cooled to room temperature, poured on ice (100 grams), transferred to a separatory funnel and extracted thrice with 100 ml diethyl ether. The organic phase was washed consecutively with 100 ml water, twice with 100 ml dilute (1.5%) sulfuric acid, 100 ml water, 100 ml concentrated sodium bicarbonate solution, and again with 100 ml water. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure, yielding 11 grams of 1-trityl-3-benzyl-sn-glycerol as a yellow oil. The yield was 94%.

Fuente