Reaktion #1372278

ord-c6025f50579b4731afb2d98ae8bbc762

Reaktionsgleichung

O
water
CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3[C@H](O)[C@@H](Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C
17α-acetoxy-6β-chloro-7α-hydroxy-1α,2α-methylene-4-pregnene-3,20-dione
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid
COC(OC)OC
trimethyl orthoformate
→
CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C
17α-acetoxy-6-chloro-1α,2α-methylene-4,6-pregnadiene-3,20-dione
Ausbeute 100.1%

Edukte

O
water
CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3[C@H](O)[C@@H](Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C
17α-acetoxy-6β-chloro-7α-hydroxy-1α,2α-methylene-4-pregnene-3,20-dione
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid
COC(OC)OC
trimethyl orthoformate

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThen the organic phase is separated
  2. 2
    Trocknendried with sodium sulfate
  3. 3
    Einengenconcentrated in vacuo

Vorschrift

5.0 g of 17α-acetoxy-6β-chloro-7α-hydroxy-1α,2α-methylene-4-pregnene-3,20-dione is mixed in 25 ml of dichloromethane with 0.1 g of p-toluenesulfonic acid and 3.0 ml of trimethyl orthoformate. The mixture is allowed to stand for 4 hours at 0° C., mixed with 20 ml of water and stirred for 15 minutes. Then the organic phase is separated, dried with sodium sulfate and concentrated in vacuo. Thus, 4.8 g of 17α-acetoxy-6-chloro-1α,2α-methylene-4,6-pregnadiene-3,20-dione with a melting point of 202° to 205° C. (80% purity) is obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04565657uspto-grants-1986_01