HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → (1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl)-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Reactant | HCID 14674517 | HCID 14674517 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (1S,5R,6R,7R)-6-(3,3-ethylenedioxyoctyl)-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one | HCID 14674520 | — |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05426115 |
| Source dataset | uspto-grants-1995_06 |
| ORD ID | ord-6d47b3eb15aa48628a928ca6cb40ca21 |
| Source note | uspto-grants-1995_06 |