Реакция #68810

Уравнение реакции

imidazole

tert-butyldimethylsilyl chloride

2-bromoethanol

Water

→

liquid

Выход 97.0%

2-(tert-Butyldimethylsilyloxy)ethyl bromide

Выход 97.0%

Растворители

DMF

diethyl ether

Условия реакции

Обработка

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

Методика

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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