Benzoyl Peroxide → HCID 86746917, compound

HRID 1587022Notes

Reaction equation

HRID 1587022 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][C@H:17]([O:24][C:25](=[O:27])[CH3:26])[C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:28]([CH3:44])[CH2:29][CH:30]=[C:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:6]1)(=[O:3])[CH3:2].BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][C@H:17]([O:24][C:25](=[O:27])[CH3:26])[C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:28](=[CH2:44])[CH2:29][CH:30]=[C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 86746915HCID 86746915, compound

Product 1

HCID 86746917HCID 86746917, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3α, 12α-diacetoxy-17β-[(1,1-diphenyl)-1-penten-4-yl]-5β-androstane (7.24 g), N-bromosuccinimide (2.26 g) and benzoyl peroxide (0.256 g) in anhydrous carbon tetrachloride (250 ml) is stirred at reflux, while being illuminated with a 275-watt sun lamp, for about 45 minutes. The mixture is cooled, filtered, and concentrated in vacuo. The resulting oil is dissolved in anhydrous pyridine (12.2 ml), the solution refluxed for about 1 hour, and concentrated in vacuo. The residue is dissolved in ether, filtered, and the ether solution washed with dilute sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is used, without further treatment, for the next step.

Workup

  1. temperatureat reflux
  2. customwhile being illuminated with a 275-watt sun lamp, for about 45 minutes
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting oil is dissolved in anhydrous pyridine (12.2 ml)
  7. temperaturethe solution refluxed for about 1 hour
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue is dissolved in ether
  10. filtrationfiltered
  11. washthe ether solution washed with dilute sodium chloride solution
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fff185621144e65882a941b449b5603
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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