m-Chloroperbenzoic acid → HCID 86733314, compound

HRID 1606385Notes

Reaction equation

HRID 1606385 reaction equation
[CH3:1][C:2]1[CH2:21][C@@H:20]2[C@:7]([CH3:24])([CH2:8][C:9](=[O:23])[C@H:10]3[C@H:19]2[CH2:18][CH2:17][C@@H:16]2[C@:11]3([CH3:22])[CH2:12][CH:13]=[CH:14][CH2:15]2)[C:3]=1[C:4](=[O:6])[CH3:5].ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)Cl>[O:33]1[C@H:14]2[CH2:15][C@H:16]3[C@:11]([CH3:22])([CH2:12][C@@H:13]12)[C@@H:10]1[C@H:19]([C@H:20]2[C@:7]([CH3:24])([CH2:8][C:9]1=[O:23])[C:3]([C:4](=[O:6])[CH3:5])=[C:2]([CH3:1])[CH2:21]2)[CH2:18][CH2:17]3

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86733315HCID 86733315, compound

Product 1

HCID 86733314HCID 86733314, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

16-Methyl-5α-pregna-2,16-diene-11,20-dione (800 mg.) in methylene chloride (50 ml.) was treated with m-chloroperbenzoic acid (85%; 535 mg.), and the solution was left to stand at room temperature overnight. More methylene chloride (50 ml.) was added and the solution washed with potassium bicarbonate solution (5%, 100 ml.) and with water (100 ml.), dried over sodium sulphate and evaporated to a crystalline solid (~ 1g.) which was purified by preparative TLC in ethyl acetate/petrol, 1/1 run twice. The main band yielded a white solid (650 mg.) which was recrystallised from acetone/ petrol to give title compound (515 mg.) as white crystals, m.p. 155°-157°, [α]D + 57.8° (c 0.9), λmax. (EtOH) 246.5 nm (ε 9150).

Workup

  1. waitthe solution was left
  2. washthe solution washed with potassium bicarbonate solution (5%, 100 ml.) and with water (100 ml.)
  3. dry with materialdried over sodium sulphate
  4. customevaporated to a crystalline solid (~ 1g.) which
  5. customwas purified by preparative TLC in ethyl acetate/petrol
  6. customThe main band yielded a white solid (650 mg.) which
  7. customwas recrystallised from acetone/ petrol

Sources & evidence

ORD record
ord-88d19219a399433c892b949a577c45b6
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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