m-Chloroperbenzoic acid → HCID 86733310, compound

HRID 1606379Notes

Reaction equation

HRID 1606379 reaction equation
[CH3:1][C:2](=[O:22])[C:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][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=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[O:31]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][CH2:18]1)[C:3]([C:2](=[O:22])[CH3:1])=[CH:4][CH2:5]2)[CH2:8][CH2:9]3

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54071661HCID 54071661, compound

Product 1

HCID 86733310HCID 86733310, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

5α-Pregna-2,16-dien-20-one (3.0 g.) in chloroform (50 ml.) was treated with m-chloroperbenzoic acid (85%, 2.0 g.). The solution was stirred at room temperature overnight, diluted with more chloroform (50 ml.), washed with dilute potassium bicarbonate solution and with water, dried over sodium sulphate and evaporated to an oil which crystallised on standing. Recrystallisation from ethyl acetate/petrol gave title compound (2.75 g.) as colourless plates, m.p. 145°-149° [α]D + 74.5°, λmax. 238 nm (ε 8970).

Workup

  1. washwashed with dilute potassium bicarbonate solution and with water
  2. dry with materialdried over sodium sulphate
  3. customevaporated to an oil which
  4. customcrystallised
  5. customRecrystallisation from ethyl acetate/petrol

Sources & evidence

ORD record
ord-70d28db832b54b9c92cffe363394d819
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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