p-Toluenesulfonic acid → 3-Ethoxy-androsta-3,5-dien-17-one

HRID 1680131Notes

Reaction equation

HRID 1680131 reaction equation
[CH3:1][C@:2]12[CH2:21][CH2:20][C@H:19]3[C@@H:8]([CH2:9][CH2:10][C:11]4[C@:17]3([CH3:18])[CH2:16][CH2:15][C:13](=[O:14])[CH:12]=4)[C@@H:7]1[CH2:6][CH2:5][C:3]2=[O:4].C(OCC)(OCC)O[CH2:24][CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:24]([O:14][C:13]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C:11](=[CH:10][CH2:9][C@@H:8]3[C@@H:19]2[CH2:20][CH2:21][C@@:2]2([CH3:1])[C@H:7]3[CH2:6][CH2:5][C:3]2=[O:4])[CH:12]=1)[CH3:25]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6128AndrostenedioneHCID 31214Ethyl orthoformate

Product 1

HCID 103582913-Ethoxy-androsta-3,5-dien-17-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Androstenedione (5 g.) was dissolved in dry benzene (20 ml). Triethyl orthoformate (6 ml) was added, followed by p-toluenesulphonic acid (250 mg) and the solution left at room temperature for ten minutes. The benzene solution was washed with aqueous sodium hydroxide (10%), followed by water, dried (anhydrous Na2SO4) and evaporated under reduced pressure to give a pale yellow solid (5.5 g.). This solid was recrystallized from ethanol to give 3-ethoxy-androsta-3,5-dien-17-one (4.3 g.) as white needles, m.p. 146°-149°. ##STR13##

Workup

  1. waitthe solution left at room temperature for ten minutes
  2. washThe benzene solution was washed with aqueous sodium hydroxide (10%)
  3. dry with materialdried (anhydrous Na2SO4)
  4. customevaporated under reduced pressure
  5. customto give a pale yellow solid (5.5 g.)
  6. customThis solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-e5461cb5d5f2418eb3753397ee250331
Source dataset
uspto-grants-1981_06
Patent number
US04272445

Reaction notes

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