HuagongsheHuagongshe Chemistry Print Report · For research reference only
Decanoyl chloride → (8R,9S,10R,13S,14S,17S)-13-ethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl decanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Decanoyl chloride | HCID 66982 | — |
| Reactant | Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)- | HCID 10039774 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | (8R,9S,10R,13S,14S,17S)-13-ethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl decanoate | HCID 44626081 | 50.1% |
Reaction Steps
Add decanoyl chloride (1.9 g.) to 13β-ethyl-17β-hydroxy-gon-4-en-3-one (1.3 g.) in pyridine (12.5 cc.) and allow the mixture to stand at room temperature overnight. Pour the mixture in 2N hydrochloric acid and extract with ether. Wash, dry and evaporate the extracts and recrystallize the residue from benzene-hexane to give the title compound (1.0 g.), m.p. 97°-97.5°; ultraviolet absorption peak at 239 mμ (ε16,500); infrared absorption peaks at 5.74; 5.99, 6.17 μ.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US03959322 |
| Source dataset | uspto-grants-1976_05 |
| ORD ID | ord-26ff28a40a344a6a84d5c76a985b2805 |
| Source note | uspto-grants-1976_05 |