4-Hydroxybenzaldehyde → 4-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

HRID 497518ノート

反応式

HRID 497518 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>ClCCl>[C:10]([Si:14]([CH3:16])([CH3:15])[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:13])([CH3:12])[CH3:11]

参加物

5

反応物 3

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde収率 75.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-Hydroxybenzaldehyde (5.14 g, 42.1 mmol) was added to a suspension of tert-butyl-dimethyl-silyl chloride (6.7 g, 44.4 mmol) and imidazole (3.03 g, 44.5 mmol) in dichloromethane (100 ml) under an atmosphere of nitrogen at room temperature. The reaction mixture was stirred at room temperature for 18 hours, and then washed sequentially with 1 M hydrochloric acid (2-fold 50 ml) followed by a saturated aqueous solution of sodium hydrogen carbonate (50 ml). The organic phase was separated, dried over anhydrous magnesium sulphate and the solvent removed in vacuo. The residual yellow oil was passed through a plug of silica gel eluting with 1:1, by volume, dichloromethane:pentane giving 4-(tert-butyl-dimethyl-silanyloxy)-benzaldehyde (7.5 g) as a golden yellow oil.

後処理

  1. washwashed sequentially with 1 M hydrochloric acid (2-fold 50 ml)
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-190706c25352454bad5a6a8cc2ac982a
出典データセット
uspto-grants-2005_09
特許番号
US06949573B2

反応ノート

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