9alpha-Hydroxyandrost-4-ene-3,17-dione → 9-Dehydroandrostenedione

HRID 1704676Notes

Reaction equation

HRID 1704676 reaction equation
O[C@:2]12[CH2:19][CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:20])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=1>CS(O)(=O)=O>[CH3:17][C@:16]12[CH2:18][CH:19]=[C:2]3[C@@H:11]([CH2:10][CH2:9][C:8]4[C@:3]3([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=4)[C@@H:12]1[CH2:13][CH2:14][C:15]2=[O:20]

Participants

3

Reactant 1

HCID 104250179alpha-Hydroxyandrost-4-ene-3,17-dione

Product 1

HCID 2395959-Dehydroandrostenedione

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

9α-Hydroxyandrostenedione (.302 g.) is stirred in methanesulfonic acid (3.0 ml.) at 25°. After 80 minutes the reaction is quenched by addition of water (15 ml.). The solids are stirred for 2 hours at 35°, collected, air-dried overnight to give androsta-4,9(11)-diene-3,17-dione, 0.272 g. (95.6% chemical yield).

Workup

  1. customAfter 80 minutes the reaction is quenched by addition of water (15 ml.)
  2. customcollected
  3. customair-dried overnight

Sources & evidence

ORD record
ord-a8e48544200e47a2ab98ede7776c8855
Source dataset
uspto-grants-1978_11
Patent number
US04127596

Reaction notes

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