Cyclohexanone → HCID 68143291, compound

HRID 1415050Notes

Reaction equation

HRID 1415050 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:21][CH3:22])[CH2:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:23])[CH3:2].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@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:21][CH3:22])[CH2:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:23])[CH3:2]

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 11143Aluminum isopropoxideHCID 24436Sodium SulfateHCID 68144451HCID 68144451, compound

Product 1

HCID 68143291HCID 68143291, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Dissolve dl-13-ethyl-3-methoxy-6-methylgona-2,5(10)-dien-17β-ol (5.5 g) in toluene (200 ml) containing cyclohexanone (70 ml) and treat with aluminum isopropoxide (4.0 g) in toluene (50 ml). Reflux under nitrogen for 2.5 hours, then add water (10 ml) followed by anhydrous sodium sulfate (5 g). Stir the suspension for 0.5 hour, filter, and wash the filter cake with benzene. Remove the solvents and concentrate the residue at 100° under vacuum (.02 mm). Triturate the crystalline residue with ice-cold methanol to obtain dl-13β-ethyl-6-methyl-3-methoxygona-2,5(10)-dien-17-one (3.6 g), m.p. 118°-125°; infrared absorption peaks (potassium bromide) at 5.78 μ, 5.90 μ, 6.00 μ, no selective ultraviolet absorption above 220 mμ.

Workup

  1. temperatureReflux under nitrogen for 2.5 hours
  2. filtrationfilter
  3. washwash the filter cake with benzene
  4. customRemove the solvents
  5. concentrationconcentrate the residue at 100° under vacuum (.02 mm)
  6. customTriturate the crystalline residue with ice-cold methanol

Sources & evidence

ORD record
ord-76114910fa1d425086ac78704e136270
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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