反応 #48868

反応方程式

Triisopropylsilyl chloride

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

imidazole

→

title compound

収率 76.7%

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

収率 76.7%

溶媒

DMF

反応条件

後処理

1. 1
   その他the internal temperature below 15° C
2. 2
   その他The reaction was quenched with 1M hydrochloric acid/diethyl ether (300 mL/800 mL)
3. 3
   その他The organic layer was separated
4. 4
   洗浄washed with 1M hydrochloric acid
5. 5
   乾燥The organic layer was dried (MgSO4)
6. 6
   ろ過filtered
7. 7
   その他evaporated
8. 8
   その他Purification
9. 9
   workup.DISTILLATIONby distillation at 10 mmHg, 90-104° C.

実験手順

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).

出典