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

HRID 1427592노트

반응식

HRID 1427592 반응식
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]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 8011HydracrylonitrileHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

HCID 105355293-((tert-Butyldimethylsilyl)oxy)propanenitrile수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-556c145e6fe649849b0ed8d630a7b53b
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933232B2

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