HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylene Glycol → 3-Hydroxy-5beta-estran-17-one ethylene ketal
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Reactant | 3-Hydroxy-5betaestran-17-one | HCID 22795659 | — |
| Solvent | Benzene | HCID 241 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-Hydroxy-5beta-estran-17-one ethylene ketal | HCID 86760179 | 94.8% |
Reaction Steps
Compound 4(10 g, 36.2 mmol) was dissolved in dry benzene (150 ml) mixed with ethylene glycol (25 ml, 280 mmol) and pyridinium p-toluenesulfonate (1 g, 3.9 mmol) and refluxed using a Dean-stark separator overnight till no starting material was detected by TLC. The cold solution was diluted with EtOAc (100 ml), washed twice with brine, dried on Na2SO4 and the solvents removed under reduced pressure. Flash-chromatography on silica gel with EtOAc: Hexane 4:6 as eluant to give 11.0 g (94.5% yield) the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07087590B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-faa2f348d6f5478eb5c5bd468fd5e72f |
| Source note | uspto-grants-2006_08 |