Methanol → 4-Nitroandrost-4-ene-3,17-dione

HRID 1604098Notes

Reaction equation

HRID 1604098 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][CH2:9]3.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CO>CC(C)=O>[N+:22]([C:12]1[C:13](=[O:21])[CH2:14][CH2:15][C@@:16]2([CH3:17])[C:11]=1[CH2:10][CH2:9][C@@H:8]1[C@@H:18]2[CH2:19][CH2:20][C@@:3]2([CH3:4])[C@H:5]1[CH2:6][CH2:7][C:2]2=[O:1])([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 11121164HCID 11121164, compoundHCID 131709961Jones' reagent

Product 1

HCID 158388964-Nitroandrost-4-ene-3,17-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 17β-hydroxy-4-nitroandrost-4-en-3-one (4-nitrotestosterone, 10.56 g, 31.7 mM) in acetone (900 ml) cooled to -6° C. is treated with Jones reagent (10.0 ml). After the excess reagent is decomposed with methanol, the solids are removed by filtration. The filtrate is concentrated, for example on a rotary evaporator under vaccum, then purified by flash chromatography on silica gel to give 4-nitroandrost-4-ene-3,17-dione, m.p. 205-205.5° C. dec.(acetone-hexane).

Workup

  1. customthe solids are removed by filtration
  2. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3af65447c2ed48a18cbc0dc752726c46
Source dataset
uspto-grants-1999_11
Patent number
US05990328

Reaction notes

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