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

HRID 1013327

反応式

HRID 1013327 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e87f74e273584391b095521f37b551f3
出典データセット
uspto-grants-2011_07
特許番号
US07981883B2

関連ノート

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