HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxychloride → 21-Acetoxy-17alpha-hydroxy-6-methylene-4-pregnene-3,20-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 11-Deoxycortisol 21-acetate | HCID 101816 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Diethoxymethane | HCID 10024 | — |
| Product | 21-Acetoxy-17alpha-hydroxy-6-methylene-4-pregnene-3,20-dione | HCID 12951790 | 86.3% |
Reaction Steps
Analogously to Example 35, 1.0 g of 21-acetoxy-17α-hydroxy-4-pregnene-3,20-dione is stirred with a suspension of 1.0 g of sodium acetate in 30 ml of chloroform, 30 ml of formaldehyde diethylacetal, and 3.8 ml of phosphorus oxychloride for 7 hours at 65° C., and then worked up. The crude product is purified on 220 g of silica gel with a methylene chloride/acetone gradient (0-12% acetone), thus obtaining 890 mg of 21-acetoxy-17α-hydroxy-6-methylene-4-pregnene-3,20-dione, mp 194.5°-196° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04322349 |
| Source dataset | uspto-grants-1982_03 |
| ORD ID | ord-05aefbe577c449cfbe499daa621feb4b |
| Source note | uspto-grants-1982_03 |