m-Chloroperbenzoic acid → HCID 86736871, compound

HRID 1701446Notes

Reaction equation

HRID 1701446 reaction equation
[Cl:1][CH2:2][C:3]([O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[C@H:16]2[C@H:7]1[C@:8]1([CH3:27])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][CH:11]=[CH:10][CH2:9]1)=[O:4].ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)(Cl)Cl>[Cl:1][CH2:2][C:3]([O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[C@H:16]2[C@H:7]1[C@:8]1([CH3:27])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][C@@H:11]2[O:36][C@@H:10]2[CH2:9]1)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86736872HCID 86736872, compound

Product 1

HCID 86736871HCID 86736871, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

11β-Chloroacetoxy-5α-pregn-2-en-20-one (1.25 g) in chloroform (50 ml) was treated with m-chloroperbenzoic acid (85%; 700 mg) and the solution was stirred at room temperature for 4 hours. Chloroform (50 ml) was added, and the solution was washed with potassium bicarbonate solution and with water; it was then dried over sodium sulphate and evaporated to a white foam which was triturated with ether to give title compound (1.05 g) as colourless prisms, m.p. 163°-169°, [α]D +107°.

Workup

  1. washthe solution was washed with potassium bicarbonate solution and with water
  2. dry with materialit was then dried over sodium sulphate
  3. customevaporated to a white foam which
  4. customwas triturated with ether

Sources & evidence

ORD record
ord-c6bfa60a68814cea9e94e979987f07f3
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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