Imidazole → 4-(Tert-butyldimethylsilyloxy)-phenyl-acetonitrile

HRID 907080노트

반응식

HRID 907080 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C)C=O.O>[Si:16]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 265484-Hydroxybenzyl cyanideHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

HCID 183335824-(Tert-butyldimethylsilyloxy)-phenyl-acetonitrile수율 84.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of (4-hydroxyphenyl)acetonitrile (6.01 g, 45.1 mmol) in N,N-dimethylformamide (60 ml) was treated with imidazole (3.81 g, 58.6 mmol), tert-butyldimethylsilyl chloride (7.49 g, 49.6 mmol) and N,N-dimethylaminopyridine (20 mg) and the resulting solution left to stir at room temperature under a nitrogen atmosphere for 16 hours. The reaction mixture was diluted with water (200 ml) and extracted with ethyl acetate (200 ml×2). The combined organic extracts were washed with sat. aq. sodium chloride (200 ml), dried (sodium sulfate) and the solvent removed in vacuo. Purification by column chromatography on silica gel eluting with ethyl acetate:pentane (0:100 changing to 10:90) gave the title compound as a pale yellow oil (9.44 g).

후처리

  1. waitthe resulting solution left
  2. extractionextracted with ethyl acetate (200 ml×2)
  3. washThe combined organic extracts were washed with sat. aq. sodium chloride (200 ml)
  4. dry with materialdried (sodium sulfate)
  5. customthe solvent removed in vacuo
  6. customPurification by column chromatography on silica gel eluting with ethyl acetate:pentane (0:100 changing to 10:90)

출처 및 근거

ORD 기록
ord-39653151c654453c80604b48b9d9c4ae
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013019B2

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