Imidazole → 1-(4-((tert-Butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)ethanone

HRID 1792973ノート

反応式

HRID 1792973 の反応式
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14].[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1>CN(C)C=O>[CH3:14][O:13][C:3]1[CH:4]=[C:5]([C:10](=[O:12])[CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[O:1][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

参加物

5

反応物 3

HCID 795ImidazoleHCID 17198AcetosyringoneHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 220255931-(4-((tert-Butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)ethanone収率 81%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Ex-59A: To a solution of 4′-hydroxy-3′,5′-dimethoxyacetophenone (1 g, 5.1 mmol) in N,N-dimethylformamide were added tert-butyldimethylsilyl chloride (1,15 g, 7.6 mmol) and imidazole (0.69 g, 10.2 mmol). The mixture was stirred at room temperature overnight. Upon quenching with 1 M sulfuric acid solution, the mixture was extracted with dichloromethane. The organic phase was washed with saturated sodium bicarbonate and brine. It was dried and evaporated. Water (2 mL) was added to the residue, and the precipitate was filtered out and dried over an oil pump to give 1.28 g (81%) of 3′,5′-dimethoxy-4′-(tert-butyldimethylsiloxy)acetophenone as a white solid, m.p. 90-92° C.

後処理

  1. customUpon quenching with 1 M sulfuric acid solution
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic phase was washed with saturated sodium bicarbonate and brine
  4. customIt was dried
  5. customevaporated
  6. additionWater (2 mL) was added to the residue
  7. filtrationthe precipitate was filtered out
  8. customdried over an oil pump

出典と根拠

ORDレコード
ord-2095895f6d47499b941b0e13f624eeae
出典データセット
uspto-grants-2006_07
特許番号
US07078431B2

反応ノート

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