Réaction #50198

ord-6d47b3eb15aa48628a928ca6cb40ca21

Équation de réaction

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
C1=COCCC1
dihydropyran
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid
→
CCCCCC1(CC[C@@H]2[C@H]3CC(=O)O[C@H]3C[C@H]2OC2CCCCO2)OCCO1
title compound ( 59 )
CCCCCC1(CC[C@@H]2[C@H]3CC(=O)O[C@H]3C[C@H]2OC2CCCCO2)OCCO1
(1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl)-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one

Réactifs

—
resultant mixture
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
C1=COCCC1
dihydropyran
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid

Réactifs

Aucun

Solvants

ClCCl
dichloromethane

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwere added
  2. 2
    AutreThe crude product obtained
  3. 3
    workup.ADDITIONby treating in the conventional manner

Mode opératoire

A solution of (1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl)-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one (6a) (4.70 g) in dichloromethane (200 ml) was cooled on ice and dihydropyran (2.41 g) and p-toluenesulfonic acid (0.23 g) were added thereto and the resultant mixture was stirred for 1,5 hours. The crude product obtained by treating in the conventional manner was subjected to silica gel column chromatography to give the title compound (59).

Source

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