Imidazole → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 40532

反応式

HRID 40532 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane収率 97%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

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.

後処理

  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)

出典と根拠

ORDレコード
ord-92442a17ea5244309ef8f7e03d77d7bd
出典データセット
uspto-grants-2013_09
特許番号
US08530459B2

関連ノート

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