تفاعل #50198

ord-6d47b3eb15aa48628a928ca6cb40ca21

معادلة التفاعل

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

المتفاعلات

—
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

الكواشف

لا شيء

المذيبات

ClCCl
dichloromethane

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05426115uspto-grants-1995_06