m-Chloroperbenzoic acid → HCID 86733293, compound

HRID 1606374Notes

Reaction equation

HRID 1606374 reaction equation
[CH3:1][C:2](=[O:23])[C:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([C:18](=[O:22])[CH2:19]2)[C@:15]2([CH3:16])[C@H:10]([CH2:11][CH:12]=[CH:13][CH2:14]2)[CH2:9][CH2:8]3)[CH2:5][CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:29]>C(Cl)(Cl)Cl>[O:29]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@:20]([CH3:21])([CH2:19][C:18]1=[O:22])[C:3]([C:2](=[O:23])[CH3:1])=[CH:4][CH2:5]2)[CH2:8][CH2:9]3

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12796452HCID 12796452, compound

Product 1

HCID 86733293HCID 86733293, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 5α-pregna- 2,16 -diene-11,20-dione (2.5 g.) in chloroform (50 ml.) was added m-chloroperoxybenzoic acid (85%, 1.8 g.), and the mixture was stirred at room temperature overnight. More chloroform was then added, and the solution was washed with dilute sodium bicarbonate solution and with water, dried over magnesium sulphate and evaporated to an oil which was triturated with ether/petrol to give title compound (1.9 g.) as colourless needles, m.p. 154°-156° , [α]D + 100°.

Workup

  1. washthe solution was washed with dilute sodium bicarbonate solution and with water
  2. dry with materialdried over magnesium sulphate
  3. customevaporated to an oil which
  4. customwas triturated with ether/petrol

Sources & evidence

ORD record
ord-6e5ded4c2ed247b99c6420b42e99662f
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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