Reacción #48868

Ecuación de reacción

Triisopropylsilyl chloride

(2R)-propane-1,2-diol

imidazole

→

title compound

Rendimiento 76.7%

(2R)-1-[(Triisopropylsilyl)oxy]propan-2-ol

Rendimiento 76.7%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe internal temperature below 15° C
2. 2
   OtroThe reaction was quenched with 1M hydrochloric acid/diethyl ether (300 mL/800 mL)
3. 3
   OtroThe organic layer was separated
4. 4
   Lavadowashed with 1M hydrochloric acid
5. 5
   SecadoThe organic layer was dried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   OtroPurification
9. 9
   workup.DISTILLATIONby distillation at 10 mmHg, 90-104° C.

Procedimiento

Triisopropylsilyl chloride (83.8 mL, 390 mmol) was added slowly over 15 minutes to a solution of (2R)-propane-1,2-diol (29.7 g, 390 mmol) in DMF at 0° C. (100 mL) keeping the internal temperature below 15° C. This was followed by addition of imidazole (66.4 g, 975 mmol) and the reaction mixture was allowed to warm to RT and stirred under argon for 20 hours. The reaction was quenched with 1M hydrochloric acid/diethyl ether (300 mL/800 mL). The organic layer was separated and washed with 1M hydrochloric acid followed by saturated brine solution. The organic layer was dried (MgSO4), filtered and evaporated. Purification by distillation at 10 mmHg, 90-104° C., afforded the title compound as colourless oil (69.5 g).

Fuente