1,2-Dichloroethane → HCID 22791150, compound

HRID 1658708Notes

Reaction equation

HRID 1658708 reaction equation
[C:1]([C@:3]1([OH:24])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([C@@H:20]([F:22])[CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:23])[CH2:15][CH2:16]1)[CH:11]=[CH:10]3)#[CH:2].C(Cl)CCl.ClC1C=CC=C(C(OO)=[O:37])C=1.C(O)(C)(C)C>C(OCC)(=O)C>[C:1]([C@:3]1([OH:24])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([C@@H:20]([F:22])[CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:23])[CH2:15][CH2:16]1)[C@H:11]1[O:37][C@@H:10]31)#[CH:2]

Participants

6

Reactant 4

HCID 111,2-Dichloroethane2×HCID 6386tert-ButanolHCID 70297m-Chloroperbenzoic acidHCID 22791146HCID 22791146, compound

Product 1

HCID 22791150HCID 22791150, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

750 mg. of 17α-ethinyl-11β-fluoro-17β-hydroxy-4,6-androstadien-3-one in 50 ml. of ethylene chloride is combined with 1.2 g. of m-chloroperbenzoic acid in 5 ml. of tert.-butanol and 1 ml. of ethylene chloride. The mixture is agitated at room temperature for 21 hours. The solution is then diluted with ethyl acetate and washed successively with sodium bisulfite solution and water. In this way, 420 mg. of 17α-ethinyl-6α,7α-epoxy-11β-fluoro-17β-hydroxy-4-androsten-3-one is isolated. UV: ε239 = 16,300 (methanol).

Workup

  1. washwashed successively with sodium bisulfite solution and water

Sources & evidence

ORD record
ord-7d857957c39b4d298183026c13655e27
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

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