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

HRID 468048Notes

Reaction equation

HRID 468048 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-c308f568dce248b096707dfa94d3dbb9
Source dataset
uspto-grants-2014_01
Patent number
US08623895B2

Reaction notes

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