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

HRID 396589

반응식

HRID 396589 반응식
[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]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 17198AcetosyringoneHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c03af725dbb419fb4274aa53f163c55
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608101B1

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