Cyclohexanone → HCID 68143291, compound

HRID 1077217Notes

Reaction equation

HRID 1077217 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-]>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: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

5

Reactant 3

HCID 7967CyclohexanoneHCID 11143Aluminum isopropoxideHCID 68144451HCID 68144451, compound

Product 1

HCID 68143291HCID 68143291, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Reflux dl-13-ethyl-3-methoxy-6-methylgona-2,5(10)-dien-17β-ol (5.5 g) in toluene (200 cc) and cyclohexanone (70 cc) with aluminum isopropoxide (4.0 g) for 2.5 hours. Add water and anhydrous sodium sulfate, filter and isolate the crude product. Triturate with ice cold methanol to obtain dl-13-ethyl-3-methoxy-6-methylgona-2,5(10)-dien-17-one (3.6 g), m.p. 118°-125°, λ max. KBr 5.78 μ, 5.90 μ, 6.0 μ. An analytical sample recrystallized from methanol has m.p. 163°-166°.

Workup

  1. filtrationAdd water and anhydrous sodium sulfate, filter
  2. customisolate the crude product
  3. customTriturate with ice cold methanol

Sources & evidence

ORD record
ord-edb93ffe6ddd4aea9c47c087b14900a4
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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