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

HRID 497518노트

반응식

HRID 497518 반응식
[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]

참가 물질

5

반응물 3

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-190706c25352454bad5a6a8cc2ac982a
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949573B2

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