Tetrahydrofuran → 21-Chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one

HRID 66549Notes

Reaction equation

HRID 66549 reaction equation
[Cl:1][C:2]([S:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25])=[C:3]=[C:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C:18](=[CH:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.C1C[O:35][CH2:34]C1.C[O-].[Na+]>CO>[Cl:1][CH:2]([S:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25])[C:3]([O:35][CH3:34])=[C:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C:18](=[CH:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 57001579HCID 57001579, compound

Product 1

HCID 5701252721-Chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21-Chloro-21-(phenylsulfinyl)pregna-4,9(11),17(20),20-tetraen-3-one, (V, Example 2, 100 mg) and THF (1 ml) are slurried and cooled to 0°-5° under nitrogen. Sodium methoxide in methanol (25%, 0.05 ml) is added with stirring. The mixture is stirred 1 hr and then quenched with water (10 ml). The mixture is extracted with ethyl acetate (2×15 ml). The organic extracts are combined, backwashed with water (10 ml), dried over sodium sulfate and concentrated under reduced pressure to give the title compound.

Workup

  1. temperaturecooled to 0°-5° under nitrogen
  2. stirringThe mixture is stirred 1 hr
  3. customquenched with water (10 ml)
  4. extractionThe mixture is extracted with ethyl acetate (2×15 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dcbf84c204bc48bd8afb3fc0c8d16176
Source dataset
uspto-grants-1982_08
Patent number
US04342702

Reaction notes

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