반응 #68810

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imidazole

tert-butyldimethylsilyl chloride

2-bromoethanol

Water

→

liquid

수율 97.0%

2-(tert-Butyldimethylsilyloxy)ethyl bromide

수율 97.0%

용매

DMF

diethyl ether

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후처리

1. 1
   기타The phases were separated
2. 2
   추출The aqueous phase was extracted with diethyl ether
3. 3
   세척The combined organic phases were washed with water and brine
4. 4
   건조The solution was dried (Na2SO4)
5. 5
   기타Evaporation of the solvent
6. 6
   workup.DISTILLATIONfollowed by bulb-to-bulb distillation (40-45° C./0.05 mmHg)

실험 절차

Following a published procedure,24 2-bromoethanol (10.0 mL, 141 mmol) was added to a mixture of imidazole (12.5 g, 184 mmol) and tert-butyldimethylsilyl chloride (21.1 g, 140 mmol) in anhydrous DMF (25 mL). The reaction mixture was stirred at room temperature for 12 h. Water and diethyl ether were added. The phases were separated. The aqueous phase was extracted with diethyl ether. The combined organic phases were washed with water and brine. The solution was dried (Na2SO4). Evaporation of the solvent followed by bulb-to-bulb distillation (40-45° C./0.05 mmHg) yielded a colorless liquid (32.5 g, 97%): IR (film, νmax cm−1) 2951, 2859, 1471; 1H NMR δ 0.07 (s, 6H), 0.89 (s, 9H), 3.36-3.41 (m, 2H), 3.85-3.90 (m, 2H); 13C NMR δ −5.06, 18.49, 26.04, 33.45, 63.74; EI-MS 137/139, 181/183, calcd 238.0389 (C8H19BrOSi); Anal. Calcd C, 40.17; H, 8.01. Found: C, 40.55; H, 8.25.

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