Imidazole → 2-(Tert-butyldimethylsilanyloxy)-1-phenylethanone

HRID 1468754Notes

Reaction equation

HRID 1468754 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17].O>CN(C)C=O>[Si:20]([O:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 135233382-(Tert-butyldimethylsilanyloxy)-1-phenylethanoneYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxyacetophenone (10 g, 74.5 mmol) and imidazole (15 g, 220 mmol) in N,N-dimethylformamide (50 ml) was added tert-butyldimethylchlorosilane (22 g, 146 mmol) at room temperature for 6 hours. The mixture was poured into water (200 ml) and extracted twice with 200 ml of ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1) to give 2-(tert-butyldimethylsilanyloxy)-1-phenylethanone (8.0 g, 31.9 mmol, 43%) as a yellow oil.

Workup

  1. extractionextracted twice with 200 ml of ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe crude product was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-6824c19322154130a704142273c1a8b9
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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