Imidazole → 3-(Tert-butyldimethylsilyloxy)propiophenone

HRID 1974501Notes

Reaction equation

HRID 1974501 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].N1C=CN=C1.CN(C)C=O>O>[Si:1]([O:9][CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 569605Hydroxypropiophenone

Product 1

HCID 135233483-(Tert-butyldimethylsilyloxy)propiophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tert-butyldimethylsilyl chloride (150 g) was added to a mixture of 3-hydroxypropiophenone (125 g), imidazole (142 g) and dimethylformamide (330 ml) and the mixture was stirred at ambient temperature for 16 hours. The mixture was poured into water (600 ml) and extracted with diethyl ether (600 ml). The organic layer was separated, washed with water (4×30 ml), dried (Na2SO4) and evaporated to give 3-(tert-butyldimethylsilyloxy)propiophenone as an oil (186 g, b.p. 114°-118° C. at 0.01 mm Hg).

Workup

  1. extractionextracted with diethyl ether (600 ml)
  2. customThe organic layer was separated
  3. washwashed with water (4×30 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-992be040f3d24b9f93e61c821cfc8ccb
Source dataset
uspto-grants-1994_02
Patent number
US05283245

Reaction notes

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