Methanol → HCID 15838897, compound

HRID 1604099Notes

Reaction equation

HRID 1604099 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[C:12]([N+:22]([O-:24])=[O:23])[C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][C@H:9]3[CH3:25].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CO>CC(C)=O>[CH3:25][C@@H:9]1[CH2:10][C:11]2[C@:16]([CH3:17])([CH2:15][CH2:14][C:13](=[O:21])[C:12]=2[N+:22]([O-:24])=[O:23])[C@@H:18]2[C@@H:8]1[C@H:5]1[C@@:3]([CH2:20][CH2:19]2)([CH3:4])[C:2](=[O:1])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 15838889HCID 15838889, compoundHCID 131709961Jones' reagent

Product 1

HCID 15838897HCID 15838897, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 17β-hydroxy-7α-methyl-4-nitroandrost-4-en-3-one (4.2 g, 12.1 mM) in acetone (400 ml) is cooled to 0° C. and is treated with Jones reagent (4.0 ml). Any excess reagent is decomposed by addition of methanol. The solids are filtered off and the filtrate is concentrated to a green solid. This material is purified by flash chromatography on silica gel to give 7α-methyl-4-nitroandrost-4-ene-3,17-dione (aqueous acetone).

Workup

  1. filtrationThe solids are filtered off
  2. concentrationthe filtrate is concentrated to a green solid
  3. customThis material is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-a5b75f1ad93947e0a517c1223fbc4c39
Source dataset
uspto-grants-1999_11
Patent number
US05990328

Reaction notes

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