Cornforth reagent → HCID 56631739, compound

HRID 652714Notes

Reaction equation

HRID 652714 reaction equation
[CH2:1]1[CH2:25][O:24][C:3]2([CH2:20][C@H:19]([CH3:21])[C@@:18]3([CH3:22])[C:5](=[CH:6][CH2:7][C@@H:8]4[C@@H:17]3[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C@@H:12]3[OH:23])[CH2:4]2)[O:2]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH2:25]1[CH2:1][O:2][C:3]2([CH2:20][C@H:19]([CH3:21])[C@@:18]3([CH3:22])[C:5](=[CH:6][CH2:7][C@@H:8]4[C@@H:17]3[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C:12]3=[O:23])[CH2:4]2)[O:24]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 70433074HCID 70433074, compound

Product 1

HCID 56631739HCID 56631739, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.6 g of 3,3-ethylenedioxy-1α-methyl-5-androsten-17β-ol is dissolved in 100 ml of dichloromethane, combined with 5.8 g of pyridinium dichromate, and agitated for 20 hours at room temperature. The reaction solution is washed with water, dried, and evaporated under vacuum. The residue is chromatographed on silica gel, thus obtaining with hexane-ethyl acetate gradients (11-16% ethyl acetate) 2.81 g of 3,3-ethylenedioxy-1α-methyl-5-androsten-17-one.

Workup

  1. washThe reaction solution is washed with water
  2. customdried
  3. customevaporated under vacuum
  4. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-6a5cda3dc810477d82bef0401d55670f
Source dataset
uspto-grants-1987_06
Patent number
US04673673

Reaction notes

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