1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Adrenosterone

HRID 1447090Notes

Reaction equation

HRID 1447090 reaction equation
Br[C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:21])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH2:4][CH2:5][C:6](=[O:22])[CH:7]=1.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>>[CH3:17][C@:16]12[CH2:18][C:19](=[O:20])[C@H:2]3[C@@H:11]([CH2:10][CH2:9][C:8]4[C@:3]3([CH3:23])[CH2:4][CH2:5][C:6](=[O:22])[CH:7]=4)[C@@H:12]1[CH2:13][CH2:14][C:15]2=[O:21]

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 111326859alpha-Bromo-11beta-hydroxy-4-androstene-3,17-dione

Product 1

HCID 223997AdrenosteroneYield 80.6%

Procedure

Under argon gas, 1 g of 9α-bromo-11β-hydroxy-4-androstene-3,17-dione is agitated in 5 ml of "Dowtherm" A for 3 minutes at 250° C. To work up the reaction mixture, the solvent is removed by steam distillation, the residue is dried and recrystallized from methylene chloride-isopropyl ether, thus obtaining 635 mg of 4-androstene-3,11,17-trione, mp 214°-216° C.

Workup

  1. customthe solvent is removed by steam distillation
  2. customthe residue is dried
  3. customrecrystallized from methylene chloride-isopropyl ether

Sources & evidence

ORD record
ord-2c3b4a462a634be3b27a2f6c4dd4d629
Source dataset
uspto-grants-1982_02
Patent number
US04315866

Reaction notes

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