Oxalyl chloride → 17beta-Chlorocarbonyl-5alpha-androst-2-en-11-one

HRID 267636Notes

Reaction equation

HRID 267636 reaction equation
[CH3:1][C@:2]12[CH2:19][C:18](=[O:20])[C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH:13]=[CH:12][CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[C:21]([OH:23])=O.C(Cl)(=O)C([Cl:27])=O>C1C=CC=CC=1>[Cl:27][C:21]([C@H:3]1[CH2:4][CH2:5][C@H:6]2[C@H:7]3[C@H:17]([C:18](=[O:20])[CH2:19][C@:2]12[CH3:1])[C@:15]1([CH3:16])[C@H:10]([CH2:11][CH:12]=[CH:13][CH2:14]1)[CH2:9][CH2:8]3)=[O:23]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 227882705alpha-Androst-2-en-11-one 17beta-carboxylic acid

Product 1

HCID 13171009417beta-Chlorocarbonyl-5alpha-androst-2-en-11-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5α-androst-2-en-11-one 17β-carboxylic acid (6.3g.) in dry benzene (200 ml.) and oxalyl chloride (15.75 ml.) was refluxed for 1.5 hr. The mixture was evaporated to give 17β-chlorocarbonyl-5α-androst-2-en-11-one as a gum which shaken with 880 ammonia (100 ml.), benzene (32 ml.) and water (32 ml.) After 1 hr. the mixture was extracted with ether. The ethereal solution was washed (H2O), dried and evaporated to give a froth. Crystallisation from chloroform/petrol afforded the title compound (1.9g.); m.p. 92°-96°; [α]D + 95.5°, (c 0.75).

Workup

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-add20113e61c4e22b2040fe11febdcaa
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

Loading…