m-Chloroperbenzoic acid → HCID 86733131, compound

HRID 267631Notes

Reaction equation

HRID 267631 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]([C:22](=[O:24])[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:33])C=1>C(Cl)(Cl)Cl>[O:33]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][C:22]1=[O:24])([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 2278825117beta-Methoxycarbonyl-5alpha-androst-2-en-11-one

Product 1

HCID 86733131HCID 86733131, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

17β-Methoxycarbonyl-5α-androst-2-en-11-one (6.63 g.) and m-chloroperbenzoic acid (4.84 g.) were stirred with chloroform (115 ml.) for 16 hours. The solution was diluted with chloroform, washed with 2% aqueous potassium hydrogen carbonate, dried (MgSO4) and evaporated to a gum. Crystallisation from ethyl acetate/light petroleum afforded pure title compound. (1.64 g.) as colourless rods; m.p. 140°-145°; [α]D + 74.2°.

Workup

  1. washwashed with 2% aqueous potassium hydrogen carbonate
  2. dry with materialdried (MgSO4)
  3. customevaporated to a gum
  4. customCrystallisation from ethyl acetate/light petroleum afforded pure title compound
  5. custom[α]D + 74.2°

Sources & evidence

ORD record
ord-f81931cf82a14d72823fe29458c47bde
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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