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

HRID 1087675

Reaction equation

HRID 1087675 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>ClS(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 24638Chlorosulfonic acidSolvent

Procedure

Following the general procedure of Example 6 but making non-critical variations, 9α-hydroxyandrostenedione (20.00 g.) is reacted with chlorosulfonic acid (10 ml.) at a reaction temperature of 1°-11°. Upon workup the reaction gives androsta-4,9(11)-diene-3,17-dione, 17.94 g., (89.7% weight yield, 95.2% chemical yield); m.p. 202°-204.5°; [α]D +217° (chloroform); UV (methanol(λmax =240 nm (ε=16,300).

Sources & evidence

ORD record
ord-247ad239e60a4909a5c8054887087c74
Source dataset
uspto-grants-1990_10
Patent number
USRE033364

Linked notes

Loading…