Reaktion #1005593

ord-73b22e193ac94ab7991c1946f13e7f02

Reaktionsgleichung

CC(=O)CO[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)C3=CC[C@]2(C)[C@@]1(O)C(=O)CCl
21-chloro-17-hydroxy-16α-(2-oxopropoxy)pregna-1,4,9(11)-triene-3,20-dione
[Cl-].[Li+]
lithium chloride
Cl
hydrogen chloride
O=C1CCC(=O)N1Cl
N-chlorosuccinimide
→
CC(=O)CO[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](Cl)C[C@]2(C)[C@@]1(O)C(=O)CCl
title compound
CC(=O)CO[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](Cl)C[C@]2(C)[C@@]1(O)C(=O)CCl
9,11β,21-Trichloro-17-hydroxy-16α-(2-oxopropoxy)pregna-1,4-diene-3,20-dione

Edukte

CC(=O)CO[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)C3=CC[C@]2(C)[C@@]1(O)C(=O)CCl
21-chloro-17-hydroxy-16α-(2-oxopropoxy)pregna-1,4,9(11)-triene-3,20-dione
[Cl-].[Li+]
lithium chloride
Cl
hydrogen chloride
O=C1CCC(=O)N1Cl
N-chlorosuccinimide

Reagenzien

Keine

Lösungsmittel

CC(=O)O
acetic acid
O
water
C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted with chloroform
  2. 2
    WaschenThe chloroform solution is washed with water
  3. 3
    Sonstigedried
  4. 4
    Sonstigeevaporated

Vorschrift

A solution of 21-chloro-17-hydroxy-16α-(2-oxopropoxy)pregna-1,4,9(11)-triene-3,20-dione (4mmoles) and 7.2 g of lithium chloride in 72 ml of glacial acetic acid is stirred at 0°-5°C and 592 mg of N-chlorosuccinimide is added. A solution of 180 mg of dry hydrogen chloride in 2.9 ml of tetrahydrofuran is added and the resulting mixture stirred at room temperature for 2 hours, poured into 400 ml of cold water, and extracted with chloroform. The chloroform solution is washed with water, dried, and evaporated to give the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US03971773uspto-grants-1976_07