Cyclohexanone → Methoxygonadiene

HRID 1414994

반응식

HRID 1414994 반응식
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20][CH3:21])[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].C1(=O)CCCCC1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O.C1(C)C=CC=CC=1>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20][CH3:21])[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:22])[CH3:2]

참가 물질

7

반응물 4

HCID 7967CyclohexanoneHCID 11143Aluminum isopropoxideHCID 24436Sodium SulfateHCID 101950(17Beta)-13-Ethyl-3-methoxygona-2,5(10)-dien-17-ol

생성물 1

HCID 102242Methoxygonadiene

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

Reflux a mixture of 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17β-ol (0.8 g.), aluminium isopropoxide (0.36 g.), toluene (26 cc.) and cyclohexanone (8 cc.) under nitrogen for 3 hours. Allow the solution to cool under nitrogen, add water (5 cc.) and shake the mixture vigorously. Add anhydrous sodium sulphate (5 g.), shake the mixture again, and then allow to stand for 30 minutes. Filter the solution, combine the filtrate with ether-washings of the residue, and evaporate, first at 30°/20 mm., then at 50°/0.1 mm. to leave as a crystalline solid 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17-one; infrared absorption peaks at 5.78, 5.92, 6.01 μ, with no absorption due to hydroxyl.

후처리

  1. temperatureReflux
  2. temperatureAllow the solution to cool under nitrogen
  3. filtrationFilter the solution
  4. customevaporate, first at 30°/20 mm
  5. customat 50°

출처 및 근거

ORD 기록
ord-d73e043756bc41bfa10a4cdffd715bb4
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04002746

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