HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → 3-Benzyloxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetra-en-17-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 3-Benzyloxy-17,17-ethylenedioxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraene | HCID 57199030 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 3-Benzyloxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetra-en-17-one | HCID 57272166 | 85.1% |
Reaction Steps
A solution of 32.8 g of 3-benzyloxy-17,17-ethylenedioxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraene in 328 ml of acetone and 32.8 ml of water is stirred at room temperature with 1.033 g of para-toluenesulfonic acid for 2 hours. Then, it is diluted with diethyl ether, washed with sodium bicarbonate and water, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane acetone. 25.4 g of 3-benzyloxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-17-one is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06271403B1 |
| Source dataset | uspto-grants-2001_08 |
| ORD ID | ord-281db49a081f45c4b84e4bdd909980c2 |
| Source note | uspto-grants-2001_08 |