Cyclohexanone → HCID 53917146, compound

HRID 1414996Notes

Reaction equation

HRID 1414996 reaction equation
[CH2:1]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C:14]4[CH2:15][CH:16]=[C:17]([O:22][CH3:23])[CH2:18][C:19]=4[CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])[CH2:2][CH2:3][CH3:4].C1(=O)CCCCC1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C:14]4[CH2:15][CH:16]=[C:17]([O:22][CH3:23])[CH2:18][C:19]=4[CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C:6]2=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 11143Aluminum isopropoxideHCID 24436Sodium SulfateHCID 53821585HCID 53821585, compound

Product 1

HCID 53917146HCID 53917146, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Reflux 13β-n-butyl-3-methoxy-gona-2,5(10)-dien-17β-ol (8 g.) in toluene (450 cc.) containing cyclohexanone (120 cc.) and aluminium isopropoxide (5 g.) under nitrogen for 4 hours. Cool, and add water (15 cc.) dropwise, followed by anhydrous sodium sulphate. Filter the mixture, wash the residue with ether and combine the filtrate and washings, dry and evaporate finally at 90°/1.05 mm. to give 13β-n-butyl-3-methoxy-gona-2,5(10)-dien-17-one (6.0 g.), m.p. 124°-128°, (from methanol); infrared absorption peaks at 5.80, 6.02 μ.

Workup

  1. temperatureCool
  2. filtrationFilter the mixture
  3. washwash the residue with ether
  4. customdry
  5. customevaporate finally at 90°/1.05 mm

Sources & evidence

ORD record
ord-b85ee5a400eb4f8490d693197fb293aa
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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