Water → 9-Dehydroandrostenedione

HRID 1704678Notes

Reaction equation

HRID 1704678 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.O>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

4

Reactant 2

HCID 962Water2×HCID 104250179alpha-Hydroxyandrost-4-ene-3,17-dione

Product 1

HCID 2395959-Dehydroandrostenedione

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

9α-Hydroxyandrostenedione (302 mg.) is added to a solution of water (2.5 ml.) in methanesulfonic acid (2.5 ml.) and heated to 100°. The mixture is slowly cooled over a period of 2 hours to 60°. Water (3 ml.) is added and the reaction mixture seeded. Work-up gives androsta-4,9(11)-diene-3,17-dione, 216 mg.(75.9% chemical yield - crude material), m.p. 170°-175°. Upon recrystallization a m.p. of 190°-194° is obtained.

Workup

  1. temperatureheated to 100°
  2. temperatureThe mixture is slowly cooled over a period of 2 hours to 60°

Sources & evidence

ORD record
ord-545193b026c0400881e28579d33edcb7
Source dataset
uspto-grants-1978_11
Patent number
US04127596

Reaction notes

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