Reaktion #354818

ord-add20113e61c4e22b2040fe11febdcaa

Reaktionsgleichung

C[C@]12CC=CC[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)O)[C@@]3(C)CC(=O)[C@@H]12
5α-androst-2-en-11-one 17β-carboxylic acid
O=C(Cl)C(=O)Cl
oxalyl chloride
→
C[C@]12CC=CC[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)Cl)[C@@]3(C)CC(=O)[C@@H]12
17β-chlorocarbonyl-5α-androst-2-en-11-one

Edukte

C[C@]12CC=CC[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)O)[C@@]3(C)CC(=O)[C@@H]12
5α-androst-2-en-11-one 17β-carboxylic acid
O=C(Cl)C(=O)Cl
oxalyl chloride

Reagenzien

Keine

Lösungsmittel

c1ccccc1
benzene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe mixture was evaporated

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US03943124uspto-grants-1976_03