Imidazole → 1-Bromo-4-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-butan-2-one

HRID 1802419Notes

Reaction equation

HRID 1802419 reaction equation
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19][CH2:20][C:21](=[O:27])[C:22]([CH3:26])([CH3:25])[CH2:23][OH:24].N1C=CN=C1>>[Br:19][CH2:20][C:21](=[O:27])[C:22]([CH3:26])([CH3:25])[CH2:23][O:24][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 59267876HCID 59267876, compound

Product 1

HCID 592679781-Bromo-4-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-butan-2-oneYield 60%

Procedure

tert-Butyldiphenylsilyl chloride (50.8 g, 184.6 mmol) is added at 0° C. to a solution of 1-bromo-4-hydroxy-3,3-dimethyl-butan-2-one (30.0 g, 153.8 mmol) and imidazole (26.0 g, 384.5 mmol). The reaction mixture is warmed to room temperature and stirred for 14 h. After adding ice water, the mixture is extracted with diethyl ether and the organic layer is dried over anhydrous Na2SO4. After filtration, removal of the solvent under reduced pressure affords the crude product that is purified by silica gel chromatography to afford 40.0 g of 1-bromo-4-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-butan-2-one as a light yellow liquid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.94 (9H, s), 1.16 (6H, s), 3.61 (2H, s), 4.80 (s, 2H), 7.38-7.58 (10H, m).

Workup

  1. extractionthe mixture is extracted with diethyl ether
  2. dry with materialthe organic layer is dried over anhydrous Na2SO4
  3. filtrationAfter filtration, removal of the solvent under reduced pressure
  4. customaffords the crude product that
  5. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-f04f08634a254b43b608030289c51358
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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