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

HRID 490846ノート

反応式

HRID 490846 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 183335824-(Tert-butyldimethylsilyloxy)-phenyl-acetonitrile収率 84.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of (4-hydroxyphenyl)acetonitrile (6.01 g, 45.1 mmol) in N,N-dimethylformamide (60 ml) was treated with imidazole (3.819, 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).

後処理

  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)

出典と根拠

ORDレコード
ord-3e35f9041f8a4582bc73286ebeb5b4dc
出典データセット
uspto-grants-2009_05
特許番号
US07528170B2

反応ノート

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