Réaction #50197

ord-ed217e2ec3674e7a8d8214038dadb11e

Équation de réaction

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

Réactifs

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

Réactifs

Aucun

Solvants

CO
methanol

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05426115uspto-grants-1995_06