Dimethylformamide → 21-Chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one
Reaction equation
Cl[C:2](=[C:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C:27](=[CH:28][CH2:29]2)[C@:25]2([CH3:26])[C:20](=[CH:21][C:22](=[O:32])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1)[CH:3]([Cl:12])[S:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].CN([CH:36]=[O:37])C.C[O-].[Na+]>CO.O>[Cl:12][CH:3]([S:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5])[C:2]([O:37][CH3:36])=[C:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C:27](=[CH:28][CH2:29]2)[C@:25]2([CH3:26])[C:20](=[CH:21][C:22](=[O:32])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
20,21-Dichloro-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one (VII, Example 2, 1.0 g), dry DMF (20 ml) and methanol (4 ml) are stirred under nitrogen and cooled to -25°. Sodium methoxide in methanol (25%, 1 ml) is added dropwise. After 30 minutes, the mixture is quenched with water (0.33 ml) and allowed to warm to 20°-25°. The product is isolated by diluting the mixture with water and extracting with ethyl acetate. The organic layer is separated and dried over sodium sulfate and then concentrated under reduced pressure to give the title compound: NMR (CDCl3) 0.85, 0.87, 0.98, 1.36, 1.34, 3.89, 3.84, 5.03, 5.10, 5.23, 5.43, 5.53, 5.72, 5.75 and 7.4-8.0δ.
Workup
- temperaturecooled to -25°
- customthe mixture is quenched with water (0.33 ml)
- temperatureto warm to 20°-25°
- customThe product is isolated
- extractionextracting with ethyl acetate
- customThe organic layer is separated
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-17c5cd0f6f82463ca7700846b40e5838
- Source dataset
- uspto-grants-1982_11
- Patent number
- US04357279
Reaction notes
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