HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formaldehyde → 17beta-Hydroxy-17alpha-methyl-6-methyleneandrosta-4,15-diene-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | N-Methylanilinium trifluoroacetate | HCID 2724109 | — |
| Reactant | 17beta-Hydroxy-17alpha-methylandrosta-4,15-dien-3-one | HCID 15679136 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 17beta-Hydroxy-17alpha-methyl-6-methyleneandrosta-4,15-diene-3-one | HCID 15679149 | 43.5% |
Reaction Steps
500 mg of 17β-hydroxy-17α-methylandrosta-4,15-diene-3-one in 8.3 ml of tetrahydrofuran is stirred at 60° C. under argon with 348 mg of paraformaldehyde and 2.2 g of N-methylanilinium trifluoroacetate. After 3.5 hours, the mixture is diluted with ethyl acetate, washed with water, dried over sodium sulfate, and concentrated under vacuum. After the crude product has been chromatographed on silica gel with a pentane-diethyl ether gradient, 226 mg of 17β-hydroxy-17α-methyl-6-methyleneandrosta-4,15-diene-3-one is obtained, mp 162° C. (from isopropyl ether).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05236912 |
| Source dataset | uspto-grants-1993_08 |
| ORD ID | ord-fe0e53d39c1c416fb5965a229101d2f4 |
| Source note | uspto-grants-1993_08 |