Sodium Hydroxide → 16alpha-Fluoro-1beta,6alpha-dimethyl-7-methylenandrost-4-ene-3,17-dione

HRID 621622Notes

Reaction equation

HRID 621622 reaction equation
[F:1][C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:25])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:22])[CH2:14][C@H:15]1[CH3:21])[C@H:10]([CH3:23])[C:9]3=[CH2:24].[OH-].[Na+]>C(O)C>[F:1][C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:25])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:22])[CH2:14][C@H:15]1[CH3:21])[C@@H:10]([CH3:23])[C:9]3=[CH2:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1863203316alpha-Fluoro-1beta,6beta-dimethyl-7-methylenandrost-4-ene-3,17-dione

Product 1

HCID 1863203216alpha-Fluoro-1beta,6alpha-dimethyl-7-methylenandrost-4-ene-3,17-dioneYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A ethanol solution (10 ml) of 16α-fluoro-1β,6β-dimethyl-7-methylenandrost-4-ene-3,17-dione (344 mg), which contains 0.1N sodium hydroxide (1 ml), is heated to reflux for about 30 min. Then the ethanol is removed in vacuo and the residue taken up in benzene. The organic phase is washed to neutrality with water, dried and evaporated. The residue is submitted to chromatographic purification as described above to give the isomeric 16α-fluoro-1β,6α-dimethyl-7-methylenandrost-4-ene-3,17-dione (292 mg).

Workup

  1. temperatureis heated
  2. temperatureto reflux for about 30 min
  3. customThen the ethanol is removed in vacuo
  4. washThe organic phase is washed
  5. customdried
  6. customevaporated
  7. customThe residue is submitted to chromatographic purification

Sources & evidence

ORD record
ord-f9adf88ce575434e832c44f67914b996
Source dataset
uspto-grants-1989_04
Patent number
US04824830

Reaction notes

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