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

HRID 1792973Notes

Reaction equation

HRID 1792973 reaction equation
[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]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 17198AcetosyringoneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2095895f6d47499b941b0e13f624eeae
Source dataset
uspto-grants-2006_07
Patent number
US07078431B2

Reaction notes

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