HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → 3beta-(Tert.-butyldimethylsilyloxy)-7alpha-chloro-5,6beta-epoxy-15beta,16beta-methylene-5beta-androstan-17-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 3beta-(Tert.-butyldimethylsilyloxy)-5,6beta-epoxy-7beta-hydroxy-15beta,16beta-methylene-5beta-androstan-17-one | HCID 13075962 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Carbon Tetrachloride | HCID 5943 | — |
| Product | 3beta-(Tert.-butyldimethylsilyloxy)-7alpha-chloro-5,6beta-epoxy-15beta,16beta-methylene-5beta-androstan-17-one | HCID 13075964 | — |
Reaction Steps
126 g of 3β-(tert.-butyldimethylsilyloxy)-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-5β-androstan-17-one is dissolved in a mixture of 600 ml of methylene chloride, 600 ml of carbon tetrachloride, and 300 ml of pyridine and stirred with 193.8 g of triphenylphosphine for 2.5 hours. The mixture is then washed with water, dried over sodium sulfate, and concentrated under vacuum. Chromatography on silica gel with hexane-acetone yields 117.4 g of 3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one, mp 155.5° C. [α]D =-87° (chloroform).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04614616 |
| Source dataset | uspto-grants-1986_09 |
| ORD ID | ord-1338a2a8b7d4465a94c1fc263f3ee3bc |
| Source note | uspto-grants-1986_09 |