Imidazole → 1-(Tert-butyldimethylsilyloxy)-4-(4-methylphenyl)butan-2-one

HRID 278478Notes

Reaction equation

HRID 278478 reaction equation
[OH:1][CH2:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1.N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C=O)C>[Si:19]([O:1][CH2:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[CH:10][CH:11]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 226284831-Hydroxy-4-(p-tolyl)butan-2-one

Product 1

HCID 226285101-(Tert-butyldimethylsilyloxy)-4-(4-methylphenyl)butan-2-oneYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice cooled solution of 1-hydroxy-4-(p-tolyl)butan-2-one in DMF (5 ml) was added imidazole (264 mg, 3.88 mmol) followed by tert-butyldimethylsilyl chloride (234 mg, 1.55 mmol). After 30 minutes the ice-bath was removed and then the mixture was stirred overnight at room temperature. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate), and concentrated in vacuo. The residue was purified by silica gel (8 g) column chromatography eluting with hexane/ethyl acetate (50:1) to give 1-(tert-butyldimethylsilyloxy)-4-(4-methylphenyl)butan-2-one (350 mg, 67.9%) as a colorless oil.

Workup

  1. customAfter 30 minutes the ice-bath was removed
  2. additionThe reaction mixture was poured into water (50 ml)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel (8 g) column chromatography
  8. washeluting with hexane/ethyl acetate (50:1)

Sources & evidence

ORD record
ord-ca88f367432940d18ca164ffa34b8f08
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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