Aluminum isopropoxide → 3-Methoxy-13-propylgona-2,5(10)-dien-17-one

HRID 1414995Notes

Reaction equation

HRID 1414995 reaction equation
[CH2:1]([C@:4]12[CH2:12][CH2:11][C@@H:10]3[C:13]4[CH2:14][CH:15]=[C:16]([O:21][CH3:22])[CH2:17][C:18]=4[CH2:19][CH2:20][C@H:9]3[C@@H:8]1[CH2:7][CH2:6][C@@H:5]2[OH:23])[CH2:2][CH3:3].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C1(C)C=CC=CC=1.C1(=O)CCCCC1>[CH2:1]([C@:4]12[CH2:12][CH2:11][C@@H:10]3[C:13]4[CH2:14][CH:15]=[C:16]([O:21][CH3:22])[CH2:17][C:18]=4[CH2:19][CH2:20][C@H:9]3[C@@H:8]1[CH2:7][CH2:6][C:5]2=[O:23])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 11143Aluminum isopropoxideHCID 6814424813beta-n-Propyl-3-methoxy-gona-2,5(10)-dien-17beta-ol

Product 1

HCID 541374823-Methoxy-13-propylgona-2,5(10)-dien-17-oneYield 67.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7967CyclohexanoneSolvent

Procedure

Reflux 13β-n-propyl-3-methoxy-gona-2,5(10)-dien-17β-ol (3.0 g.) with aluminium isopropoxide in toluene and cyclohexanone according to the conditions of Oppenauer oxidation. Isolate and recrystallize the product from methanol to give 13β-n-propyl-3-methoxy-gona-2,5(10)-dien-17-one (2.0 g.), m.p. 128°-31° C. with softening at 125°.

Workup

  1. customIsolate
  2. customrecrystallize the product from methanol

Sources & evidence

ORD record
ord-26db2dfa1a554cbab259264f3476f516
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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