Methanol → HCID 10640035, compound

HRID 375514Notes

Reaction equation

HRID 375514 reaction equation
[CH:1]1([O:4][C@H:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:24])[CH2:17][CH2:18]2)=[CH:13][CH2:12]4)[CH2:3][CH2:2]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CO>CC(C)=O>[CH:1]1([O:4][C@H:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[CH2:17][CH2:18]2)[CH2:13][CH2:12]4)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1488276417beta-(Cyclopropyloxy)androst-5-en-3beta-olHCID 131709961Jones' reagent

Product 1

HCID 10640035HCID 10640035, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 17β-cyclopropyloxy-androst-5-en-3β-o1 (19.36 g, 58.9 mM) in acetone (1.9 L) previously cooled to -3° C. is treated with Jones reagent (20 ml). The excess reagent is decomposed with methanol. The solids are removed by filtration. The filtrate is concentrated to a green oil which is purified by flash chromatography on silica gel to give 17β-cyclopropyloxy-androst-4-en-3-one (11.0 g, 57%).

Workup

  1. customThe solids are removed by filtration
  2. concentrationThe filtrate is concentrated to a green oil which
  3. customis purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-34faa9f419f842a58f91b1e31abfa3e4
Source dataset
uspto-grants-1996_01
Patent number
US05486511

Reaction notes

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