3beta-Acetoxyandrost-5-en-17-one → HCID 21813599, compound

HRID 1654981Notes

Reaction equation

HRID 1654981 reaction equation
[CH3:1][C:2]([O:4][C@@H:5]1[CH2:18][C:17]2[C@@:8]([CH3:24])([C@@H:9]3[C@@H:14]([CH2:15][CH:16]=2)[C@@H:13]2[CH2:19][CH2:20][C:21](=[O:22])[C@@:12]2([CH3:23])[CH2:11][CH2:10]3)[CH2:7][CH2:6]1)=[O:3].[CH3:25][C:26](C)=[O:27].C(OC(C)=C)(=O)C>C(OC(C)=C)(=O)C.S(=O)(=O)(O)O>[C:2]([O:4][C@H:5]1[CH2:6][CH2:7][C@@:8]2([CH3:24])[C:17](=[CH:16][CH2:15][C@@H:14]3[C@@H:9]2[CH2:10][CH2:11][C@@:12]2([CH3:23])[C@H:13]3[CH2:19][CH:20]=[C:21]2[O:22][C:26](=[O:27])[CH3:25])[CH2:18]1)(=[O:3])[CH3:1]

Participants

5

Reactant 2

HCID 147093beta-Acetoxyandrost-5-en-17-oneHCID 18185689HCID 18185689, compound

Product 1

HCID 21813599HCID 21813599, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 7916Isopropenyl acetateSolvent3×

Procedure

300 g (0.9 mole) of dehydroepiandrosterone acetate are dissolved in 1160 ml of isopropenyl acetate, whereupon a solution of 4 ml of concentrated sulfuric acid in 100 ml of isopropenyl acetate is added. The temperature of the reaction mixture is raised slowly (in two hours) to the boiling temperature of isopropenyl acetate, and continuously 400 ml of an acetone/isopropenyl acetate mixture are distilled off. After heating and continuous distillation for 6 hours, the solution is cooled to room temperature and added to 10000 ml of ice water, under stirring. The precipitous solution is allowed to stand at 5° to 10° C. for 12 hours, whereupon the precipitate is filtered off, washed acid-free with water, dried at room temperature and the crude product is crystallized from methanol.

Workup

  1. additionis added
  2. distillationare distilled off
  3. temperatureAfter heating
  4. distillationcontinuous distillation for 6 hours
  5. additionadded to 10000 ml of ice water
  6. filtrationis filtered off
  7. washwashed acid-free with water
  8. customdried at room temperature
  9. customthe crude product is crystallized from methanol

Sources & evidence

ORD record
ord-3cad38c259044b4d93ccd47804a654f2
Source dataset
uspto-grants-1995_04
Patent number
US05410040

Reaction notes

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