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Cyclohexanone → Methoxygonadiene

HRID 1077176
Notes
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Reaction equation

HRID 1077176 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

HCID 102242Methoxygonadiene

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 1140TolueneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-3cc53eeb11554e89bc5362232783d719
Source dataset
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03959322

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes