تفاعل #68810

معادلة التفاعل

imidazole

tert-butyldimethylsilyl chloride

2-bromoethanol

Water

→

liquid

المردود 97.0%

2-(tert-Butyldimethylsilyloxy)ethyl bromide

المردود 97.0%

المذيبات

DMF

diethyl ether

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر