Imidazole → 3-((tert-Butyldimethylsilyl)oxy)propanenitrile

HRID 1430700ノート

反応式

HRID 1430700 の反応式
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][CH2:15][CH2:16][C:17]#[N:18]>CN(C=O)C>[Si:6]([O:14][CH2:15][CH2:16][C:17]#[N:18])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

参加物

5

反応物 3

HCID 795ImidazoleHCID 8011HydracrylonitrileHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 105355293-((tert-Butyldimethylsilyl)oxy)propanenitrile収率 75%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Imidazole (33.6 g, 495 mmol) and tert-butyldimethylsilyl chloride (27.2 g, 180 mmol) were added to a 0° C. solution of 3-hydroxypropanenitrile (10.6 g, 150 mmol) in DMF 50 mL). The mixture was allowed to warm to rt, then was stirred at rt for 12 hrs. The mixture was quenched with water (500 mL), and then extracted with EtOAc (3×). The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (gradient elution 0˜5% EtOAc/petroleum ether) to give 3-(tert-butyldimethylsilyloxy) propanenitrile (18 g, 75%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.74 (t, J=6.0 Hz, 2H), 2.43 (t, J=6.0 Hz, 2H), 0.81 (s, 9H), 0.00 (s, 6H).

後処理

  1. customThe mixture was quenched with water (500 mL)
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (gradient elution 0˜5% EtOAc/petroleum ether)

出典と根拠

ORDレコード
ord-b660658239694a03976119687c72cf3c
出典データセット
uspto-grants-2015_01
特許番号
US08940897B2

反応ノート

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