Imidazole → 1-Butanone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenyl-

HRID 270494Notes

Reaction equation

HRID 270494 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[C:13]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])([CH3:15])[CH3:14].N1C=CN=C1>CN(C=O)C.C(OCC)C>[Si:17]([O:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 109758164-Hydroxy-1-phenylbutan-1-one

Product 1

HCID 110657931-Butanone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenyl-Yield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-1-phenyl-butan-1-one (3.29 g, 20 mmol) in DMF (20 mL) was added tert-butylchlorodimethyl-silane (4.5 g, 30 mmol) and imidazole (4.1 g, 60 mmol). After stirring at room temperature for 14 hours, the reaction mixture was diluted with diethyl ether (150 mL) and washed with 1M HCl (2×70 mL), water (2×70 mL) and brine (100 mL). The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (6% ethyl acetate in hexanes) to provide the product (5 g, 90%) as a colorless oil.

Workup

  1. washwashed with 1M HCl (2×70 mL), water (2×70 mL) and brine (100 mL)
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (6% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2cc95be0583248d0af7d31808f264342
Source dataset
uspto-grants-2008_11
Patent number
US07449486B2

Reaction notes

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