Reaction #50197

ord-ed217e2ec3674e7a8d8214038dadb11e

Reaction equation

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

Reactants

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

Reagents

None

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

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.v1Patent: US05426115uspto-grants-1995_06