Cyclohexanone → HCID 68143291, compound

HRID 1415037Notes

Reaction equation

HRID 1415037 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°, λmax. 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-d543525accd0482f8e20650af871feef
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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