Chloranil → HCID 22800109, compound

HRID 1439185Notes

Reaction equation

HRID 1439185 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C@@H:15]([O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:14][CH2:13]4)[CH:10]=[CH:9][C:8]1=[CH:7][C:6](=[O:28])[CH2:5][CH2:4]2.C[O-].[Na+].OC1CC[C@@]2(CO)C(=CC=C3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2OC(=O)C(C)(C)C)C=1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C=CC=CC=1.C(O)(=O)C.CS(C)=O>[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C:11](=[C:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C@@H:15]([O:21][C:22](=[O:27])[C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:14][CH2:13]4)[CH:10]=[CH:9][C:8]1=[CH:7][C:6](=[O:28])[CH2:5][CH2:4]2

Participants

8

Reactant 4

HCID 8371ChloranilHCID 10942334Sodium MethoxideHCID 22800128HCID 22800128, compoundHCID 68122342HCID 68122342, compound

Product 1

HCID 22800109HCID 22800109, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Procedure

A solution of 200 mg. of 19-hydroxy-17β-pivaloxyandrosta-4,6-dien 3-one in 2 ml. of dimethyl sulfoxide was treated with 400 mg. of sodium methoxide under nitrogen for 15 seconds. The mixture was then poured into 20 ml. of half-frozen 10% aqueous acetic acid, stirred for a few minutes under nitrogen and filtered to yield a precipitate, which had λ max 321 mμ and consisted essentially of 3,19-dihydroxy-17β-pivaloxyandrosta-3,5, 7-triene. The latter product was then treated with an equal amount of chloranil in 20 volumes of toluene at room temperature for 10 minutes. Extraction with aqueous potassium hydroxide and evaporation afforded 19-hydroxy-17β-pivaloxyandrosta-4,6,8(14)-trien 3-one as indicated by tlc and uv-spectroscopy.

Workup

  1. additionThe mixture was then poured into 20 ml
  2. filtrationfiltered
  3. customto yield a precipitate, which
  4. extractionExtraction
  5. customwith aqueous potassium hydroxide and evaporation

Sources & evidence

ORD record
ord-70370e8425c24b9a88f41471c9d42bb7
Source dataset
uspto-grants-1977_11
Patent number
US04058539

Reaction notes

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