11beta-Trimethylsiloxy-21-acetoxy-6alpha-fluoropregna-4,16-diene-3,20-dione → 11beta-Trimethylsiloxy-21-acetoxy-6alpha-fluoropregna-1,4,16-triene-3,20-dione
Reaction equation
[CH3:1][Si:2]([CH3:33])([CH3:32])[O:3][C@H:4]1[CH2:27][C@@:26]2([CH3:28])[C@@H:15]([CH2:16][CH:17]=[C:18]2[C:19](=[O:25])[CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@H:14]2[C@H:5]1[C@:6]1([CH3:31])[C:11]([C@@H:12]([F:29])[CH2:13]2)=[CH:10][C:9](=[O:30])[CH2:8][CH2:7]1>O1CCOCC1>[CH3:33][Si:2]([CH3:1])([CH3:32])[O:3][C@H:4]1[CH2:27][C@@:26]2([CH3:28])[C@@H:15]([CH2:16][CH:17]=[C:18]2[C:19](=[O:25])[CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@H:14]2[C@H:5]1[C@:6]1([CH3:31])[C:11]([C@@H:12]([F:29])[CH2:13]2)=[CH:10][C:9](=[O:30])[CH:8]=[CH:7]1Participants
Procedure
A mixture of 3.5 g of 11β-trimethylsiloxy-21-acetoxy-6α-fluoropregna-4,16-diene-3,20-dione obtained according to Example 6, 2.65 g of 2,3-dichloro-4,5-dicyanobenzoquinone (DDQ) and 30 ml of dioxan was heated under reflux for 2 hours. The resulting dark colored suspension was cooled, filtered from dichloro-dicyanohydroquinone, and evaporated to dryness. The residue was dissolved in chloroform and passed through a short column of neutral alumina (50 g). The solvent was evaporated under reduced pressure. The residue was crystallized from methanol. The analytical sample of 11β-trimethylsiloxy-21-acetoxy-6α-fluoropregna-1,4,16-triene-3,20-dione (compound 13) was obtained by an additional recrystallization from methanol. The yield was 2.65 g.
Workup
- customobtained
- temperaturewas heated
- temperatureunder reflux for 2 hours
- temperatureThe resulting dark colored suspension was cooled
- filtrationfiltered from dichloro-dicyanohydroquinone
- customevaporated to dryness
- dissolutionThe residue was dissolved in chloroform
- customThe solvent was evaporated under reduced pressure
- customThe residue was crystallized from methanol
Sources & evidence
- ORD record
- ord-aaa86bebcf0a4c13842b1615fa50d8d5
- Source dataset
- uspto-grants-1977_07
- Patent number
- US04036831
Reaction notes
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