4-tert-Butylcyclohexanone → Cyclohexane, 1-(1,1-dimethylethyl)-4-methylene-

HRID 1013327

반응식

HRID 1013327 반응식
[CH3:1]C([O-])(C)C.[K+].[C:7]([CH:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)([CH3:10])([CH3:9])[CH3:8].[NH4+].[Cl-]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[C:7]([CH:11]1[CH2:16][CH2:15][C:14](=[CH2:1])[CH2:13][CH2:12]1)([CH3:10])([CH3:9])[CH3:8]

참가 물질

6

반응물 3

HCID 73924-tert-ButylcyclohexanoneHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 139425Cyclohexane, 1-(1,1-dimethylethyl)-4-methylene-

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 3283Diethyl Ether용매2회

실험 절차

Methyltriphenylphosphonium bromide (17.4 g, 48.6 mmol) was placed in abs. diethyl ether (106 ml) under a nitrogen atmosphere. Potassium tert-butylate (5.0 g, 45.4 mmol) was slowly added at 0° C. After 30 min, 4-tert-butylcyclohexanone (5.0 g, 32.4 mmol) as a solution in diethyl ether (10 ml) was slowly added dropwise, again at 0° C. The reaction mixture was stirred overnight at RT. For working up, the reaction mixture was cooled in an ice bath and mixed with sat. aq. NH4Cl solution. The phases were separated and the aqueous phase was shaken out several times with diethyl ether. The combined organic phases were dried over magnesium sulphate and the solvent was removed under vacuum. After column chromatography (silica gel, hexane/EtOAc 2:1), the desired compound 1-tert-butyl-4-methylenecyclohexane was obtained as a colourless liquid (3.93 g, 80% of the theoretical amount).

후처리

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. customThe phases were separated
  3. stirringthe aqueous phase was shaken out several times with diethyl ether
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. customthe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-e87f74e273584391b095521f37b551f3
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981883B2

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