m-Chloroperbenzoic acid → HCID 12796457, compound

HRID 2049472Notes

Reaction equation

HRID 2049472 reaction equation
[CH3:1][C@:2]12[CH2:19][C:18](=[O:20])[C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH:13]=[CH:12][CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)(Cl)Cl>[O:30]1[C@H:12]2[CH2:11][C@H:10]3[C@:15]([CH3:16])([CH2:14][C@@H:13]12)[C@@H:17]1[C@H:7]([C@H:6]2[C@@:2]([CH2:19][C:18]1=[O:20])([CH3:1])[C:3](=[O:21])[CH2:4][CH2:5]2)[CH2:8][CH2:9]3

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12796455HCID 12796455, compound

Product 1

HCID 12796457HCID 12796457, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5α-androst-2-ene-11,17-dione (37.2 g), m-chloroperbenzoic acid (30 g) and chloroform (600 ml) was allowed to stand for 0.5 hour at room temperature before partitioning between chloroform and saturated aqueous NaHCO3 solution. The organic phase was isolated and washed with water, dried and evaporated to a low volume. Addition of petroleum ether (b.p. 60°-80° C.) followed by refrigeration overnight afforded crystalline material (27.5 g). Recrystallisation from ethyl acetate-petroleum ether (b.p. 60°-80° C.) afforded the title compound, m.p. 166°-167°, [α]D +126°.

Workup

  1. custombefore partitioning between chloroform and saturated aqueous NaHCO3 solution
  2. customThe organic phase was isolated
  3. washwashed with water
  4. customdried
  5. customevaporated to a low volume
  6. additionAddition of petroleum ether (b.p. 60°-80° C.)
  7. waitfollowed by refrigeration overnight

Sources & evidence

ORD record
ord-85c1d9d238854fd988ba3ab16f58d84d
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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