反応 #68810

反応方程式

imidazole

tert-butyldimethylsilyl chloride

2-bromoethanol

Water

→

liquid

収率 97.0%

2-(tert-Butyldimethylsilyloxy)ethyl bromide

収率 97.0%

溶媒

DMF

diethyl ether

反応条件

後処理

1. 1
   その他The phases were separated
2. 2
   抽出The aqueous phase was extracted with diethyl ether
3. 3
   洗浄The combined organic phases were washed with water and brine
4. 4
   乾燥The solution was dried (Na2SO4)
5. 5
   その他Evaporation of the solvent
6. 6
   workup.DISTILLATIONfollowed by bulb-to-bulb distillation (40-45° C./0.05 mmHg)

実験手順

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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