Imidazole → 3-(Tert-butyldimethylsilyloxy)propiophenone

HRID 1614228Notes

Reaction equation

HRID 1614228 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>[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

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 569605Hydroxypropiophenone

Product 1

HCID 135233483-(Tert-butyldimethylsilyloxy)propiophenoneYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyldimethylsilyl chloride (22.5 g) was added to a mixture of 3-hydroxypropiophenone (18.7 g), imidazole (21.3 g) and dimethylformamide (100 ml) and the solution was stirred at ambient temperature for 6 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with an aqueous sodium chloride solution, dried (Na2SO4) and evaporated. Petrol (b.p. 60°-80° C., 250 ml) was added to the residue, the resulting mixture was filtered and the filtrate was evaporated to give 3-(tert-butyldimethylsilyloxy)propiophenone as a pale yellow oil (31 g) which was used without further purification.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with an aqueous sodium chloride solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. additionPetrol (b.p. 60°-80° C., 250 ml) was added to the residue
  8. filtrationthe resulting mixture was filtered
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-37872556cdf245069fe0dceeec8cd989
Source dataset
uspto-grants-1993_03
Patent number
US05196422

Reaction notes

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