Aluminum isopropoxide → 3-Methoxyestra-2,5(10)-dien-17-one

HRID 1415057

Reaction equation

HRID 1415057 reaction equation
[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]1[OH:21].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C1(=O)CCCCC1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]1=[O:21]

Participants

5

Reactant 2

HCID 11143Aluminum isopropoxideHCID 1019633-Methoxyestra-2,5(10)-dien-17beta-ol

Product 1

HCID 227914253-Methoxyestra-2,5(10)-dien-17-oneYield 88.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 7967CyclohexanoneSolvent

Procedure

Dissolve dl-3-methoxyestra-2,5(10)-dien-17β-ol (4 g) in cyclohexanone (40 ml) and toluene (140 ml) and add a solution of aluminum isopropoxide (4 g) in toluene (56 ml). Reflux in an atmosphere of nitrogen for two hours and cool. Add water (7.5 ml), shake, and then dry by adding sodium sulfate (10 g). Filter and evaporate under vacuum and recrystallize the residue from methanol to obtain dl-3-methoxyestra-2,5(10)-dien-17-one (3.5 g); m.p. 116°-118°; infrared absorption maxima at 5.76 μ, 5.9 μ, 6.01 μ.

Workup

  1. temperatureReflux in an atmosphere of nitrogen for two hours
  2. temperaturecool
  3. dry with materialAdd water (7.5 ml), shake, and then dry
  4. additionby adding sodium sulfate (10 g)
  5. filtrationFilter
  6. customevaporate under vacuum
  7. customrecrystallize the residue from methanol

Sources & evidence

ORD record
ord-c5457bcecc1a44e6872f38b3d07e5aa6
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Linked notes

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