Reaktion #50197

ord-ed217e2ec3674e7a8d8214038dadb11e

Reaktionsgleichung

CC(=O)O
acetic acid
CCCCCC1(CCC23CC(OC(=O)c4ccc(-c5ccccc5)cc4)CC2CC(=O)O3)OCCO1
3,3-ethylenedioxyoctyl-7-(4-phenylbenzoyloxy)-2-oxabicyclo[3.3.0]octan-3-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
CCCCCC1(CC[C@@H]2[C@H]3CC(=O)O[C@H]3C[C@H]2O)OCCO1
title compound ( 6a )
CCCCCC1(CC[C@@H]2[C@H]3CC(=O)O[C@H]3C[C@H]2O)OCCO1
(1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl)-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one

Edukte

CC(=O)O
acetic acid
—
resultant mixture
CCCCCC1(CCC23CC(OC(=O)c4ccc(-c5ccccc5)cc4)CC2CC(=O)O3)OCCO1
3,3-ethylenedioxyoctyl-7-(4-phenylbenzoyloxy)-2-oxabicyclo[3.3.0]octan-3-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude product obtained
  2. 2
    workup.ADDITIONby treating in the conventional manner

Vorschrift

To a solution of (1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl-7-(4-phenylbenzoyloxy)-2-oxabicyclo[3.3.0]octan-3-one (5a) (8.20 g) in methanol (200 ml) was added potassium carbonate (1.15 g) and the resultant mixture was stirred overnight, and acetic acid (1 ml) was added thereto. The crude product obtained by treating in the conventional manner was subjected to silica gel column chromatography to give the title compound (6a).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05426115uspto-grants-1995_06