Imidazole → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 40532

반응식

HRID 40532 반응식
[Br:1][CH2:2][CH2:3][OH:4].N1C=CN=C1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].O>CN(C=O)C.C(OCC)C>[Si:10]([O:4][CH2:3][CH2:2][Br:1])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 108982-BromoethanolHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane수율 97%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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.

후처리

  1. customThe phases were separated
  2. extractionThe aqueous phase was extracted with diethyl ether
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialThe solution was dried (Na2SO4)
  5. customEvaporation of the solvent
  6. distillationfollowed by bulb-to-bulb distillation (40-45° C./0.05 mmHg)

출처 및 근거

ORD 기록
ord-92442a17ea5244309ef8f7e03d77d7bd
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530459B2

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