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

HRID 468048노트

반응식

HRID 468048 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c308f568dce248b096707dfa94d3dbb9
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623895B2

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