反応 #50198

ord-6d47b3eb15aa48628a928ca6cb40ca21

反応方程式

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

反応物

—
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

試薬

なし

溶媒

ClCCl
dichloromethane

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05426115uspto-grants-1995_06