Reaktion #68810

Reaktionsgleichung

imidazole

tert-butyldimethylsilyl chloride

2-bromoethanol

Water

→

liquid

Ausbeute 97.0%

2-(tert-Butyldimethylsilyloxy)ethyl bromide

Ausbeute 97.0%

Lösungsmittel

DMF

diethyl ether

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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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