Pyridine → 3-(2-Ethylhexanoyloxy)-5,5-dimethyl-2-(2',4'-dimethylphenyl)-2-cyclohexenone

HRID 46791

반응식

HRID 46791 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14](=[O:15])[CH2:13][C:12]([CH3:17])([CH3:16])[CH2:11][C:10]1=[O:18].N1C=CC=CC=1.[CH2:25]([CH:27]([CH2:31][CH2:32][CH2:33][CH3:34])[C:28](Cl)=[O:29])[CH3:26]>C(Cl)(Cl)Cl>[CH2:25]([CH:27]([CH2:31][CH2:32][CH2:33][CH3:34])[C:28]([O:18][C:10]1[CH2:11][C:12]([CH3:16])([CH3:17])[CH2:13][C:14](=[O:15])[C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])=[O:29])[CH3:26]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 791032-Ethylhexanoyl chlorideHCID 125563452-(2,4-Dimethylphenyl)-5,5-dimethylcyclohexane-1,3-dione

생성물 1

HCID 136881193-(2-Ethylhexanoyloxy)-5,5-dimethyl-2-(2',4'-dimethylphenyl)-2-cyclohexenone수율 51%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of 1.50 g (6.14 mmol) of 2-(2',4'-dimethylphenyl)-5,5-dimethyl-1,3-cyclohexanedione in 10 ml of chloroform was cooled in ice and 1.94 g (24.56 mmol) of pyridine added followed by 2.00 g (12.28 mmol) of 2-ethylhexanoyl chloride. The mixture was stirred for 2 hrs. at room temperature, then refluxed for 12 hrs. The mixture was worked up exactly as described in Example I above to give 1.58 g of a slightly yellow, viscous oil. This material was chromatographed through 75 g of silica gel (0.063-0.2 mm) using a gradient ranging from 98:2 to 90:10 hexane-ethyl acetate. The chromatography gave 1.15 g (51%) of 3-(2-ethylhexanoyloxy)-5,5-dimethyl-2-(2',4'-dimethylphenyl)-2-cyclohexenone as a clear colorless oil which showed one spot on a thin layer chromatogram (70:30 hexane-ethyl acetate) at Rf=0.52.

후처리

  1. customto give 1.58 g of a slightly yellow, viscous oil
  2. customThis material was chromatographed through 75 g of silica gel (0.063-0.2 mm)

출처 및 근거

ORD 기록
ord-e64129aedeb649daadba051e8eda026b
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04175135

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