p-Toluenesulfonic acid → (1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl)-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one

HRID 2226239Notes

Reaction equation

HRID 2226239 reaction equation
[CH2:1]1[CH2:22][O:21][C:3]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([CH2:4][CH2:5][C@H:6]2[C@H:13]([OH:14])[CH2:12][C@H:11]3[C@@H:7]2[CH2:8][C:9](=[O:15])[O:10]3)[O:2]1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH2:1]1[CH2:22][O:21][C:3]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([CH2:4][CH2:5][C@H:6]2[C@H:13]([O:14][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][O:23]3)[CH2:12][C@H:11]3[C@@H:7]2[CH2:8][C:9](=[O:15])[O:10]3)[O:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 14674517HCID 14674517, compound

Product 1

HCID 14674520(1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl)-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  1. additionwere added
  2. customThe crude product obtained
  3. additionby treating in the conventional manner

Sources & evidence

ORD record
ord-852bfef20d1c4ace861d2a649d0327e3
Source dataset
uspto-grants-1994_09
Patent number
US05346921

Reaction notes

Loading…