반응 #48868

반응 방정식

Triisopropylsilyl chloride

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

imidazole

→

title compound

수율 76.7%

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

수율 76.7%

용매

DMF

반응 조건

후처리

1. 1
   기타the internal temperature below 15° C
2. 2
   기타The reaction was quenched with 1M hydrochloric acid/diethyl ether (300 mL/800 mL)
3. 3
   기타The organic layer was separated
4. 4
   세척washed with 1M hydrochloric acid
5. 5
   건조The organic layer was dried (MgSO4)
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타Purification
9. 9
   workup.DISTILLATIONby distillation at 10 mmHg, 90-104° C.

실험 절차

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).

출처