m-Chloroperbenzoic acid → HCID 86733335, compound

HRID 1606494Notes

Reaction equation

HRID 1606494 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C@H:14]([CH2:15][CH:16]=[CH:17][CH2:18]1)[CH2:13][CH2:12]3)=[O:4].ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)(Cl)Cl>[O:32]1[C@H:16]2[CH2:15][C@H:14]3[C@:19]([CH3:20])([CH2:18][C@@H:17]12)[C@@H:21]1[C@H:11]([C@H:8]2[C@@:6]([CH2:23][CH2:22]1)([CH3:7])[C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]2)[CH2:12][CH2:13]3

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86733336HCID 86733336, compound

Product 1

HCID 86733335HCID 86733335, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 17β-methoxycarbonyl-5α-androst-2-ene (7.0 g.,) and 85% m-chloroperbenzoic acid (5.0 g.) in chloroform (125 ml.) was stirred for 1.5 hr. at room temperature and then diluted with chloroform (125 ml.). This solution was washed with aqueous 10% sodium bicarbonate and water prior to drying. Filtration and evaporation afforded a solid (8.075 g.) which was recrystallised from methylene chloride/cyclohexane to afford the pure title compound; [α]D + 67°, (c, 0.8).

Workup

  1. washThis solution was washed with aqueous 10% sodium bicarbonate and water
  2. customto drying
  3. filtrationFiltration and evaporation
  4. customafforded a solid (8.075 g.) which
  5. customwas recrystallised from methylene chloride/cyclohexane

Sources & evidence

ORD record
ord-6a48965ba2994021af0d65950f8aaad0
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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