Phenylseleninyl benzeneseleninate → 566-91-6

HRID 27045Notes

Reaction equation

HRID 27045 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].C1([Se](O[Se](C2C=CC=CC=2)=O)=O)C=CC=CC=1>ClC1C=CC=CC=1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH:19]=[CH:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 87253Phenylseleninyl benzeneseleninateHCID 108835733-Oxocholestane

Product 1

HCID 164675566-91-6Yield 64%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Cholestan-3-one (100 mg) was dissolved in chlorobenzene (5 ml), benzeneseleninic anhydride (188 mg, 2 equiv.) added and the solution heated to reflux with stirring under nitrogen in the dark. After 3 hours tlc showed almost complete reaction. The mixture was allowed to cool before filtering down a short silica column, washing with petrol containing 10% methylene chloride followed by releasing the crude product by washing with methanol. On evaporation an oil (107.1 mg) was obtained which crystallised on cooling in cardice. mp. 50°-57° C. Plc of the resulting impure product yielded 63.3 mg (63%) of cholesta-1,4-dien-3-one mp. 110°-112° C. (literature melting point 112° C.). λmax. 242 nm (ε 14500) (literature U.V. absorption 242 nm (ε 15000)). I.R. spectrum identical to previously prepared pure samples. The results of several runs are tabulated below:

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux
  3. customreaction
  4. temperatureto cool
  5. filtrationbefore filtering down a short silica column
  6. washwashing with petrol containing 10% methylene chloride
  7. washby washing with methanol
  8. customOn evaporation an oil (107.1 mg)
  9. customwas obtained which
  10. customcrystallised
  11. temperatureon cooling in cardice

Sources & evidence

ORD record
ord-d87b4ca1a22b46e9b8dbacd98c521a34
Source dataset
uspto-grants-1980_09
Patent number
US04220588

Reaction notes

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