p-Toluenesulfonic acid → HCID 12800131, compound

HRID 1680132Notes

Reaction equation

HRID 1680132 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)OCC.[C:32]1(C)[CH:37]=CC(S(O)(=O)=O)=C[CH:33]=1>CC(O)C.N1C=CC=CC=1>[CH:32]([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)([CH3:37])[CH3:33]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6128AndrostenedioneHCID 31214Ethyl orthoformate

Product 1

HCID 12800131HCID 12800131, compoundYield 1,677.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 3776IsopropanolSolvent

Procedure

Androstenedione (10 g.) was dissolved in propan-2-ol (500 ml). Triethyl orthoformate (7.15 ml) was added, followed by p-toluenesulphonic acid (250 mg) and the solution refluxed for fifteen minutes. A few drops of pyridine were added and the solution evaporated under reduced pressure to give a pale yellow solid. This was recrystallised from methanol to give 3-iso-propoxy-androsta-3,5-dien-17-one (8.0 g) as white crystals, M.p. 147°-151°. ##STR14##

Workup

  1. temperaturethe solution refluxed for fifteen minutes
  2. customthe solution evaporated under reduced pressure
  3. customto give a pale yellow solid
  4. customThis was recrystallised from methanol

Sources & evidence

ORD record
ord-b6e9d8ac52e64a1db0de40c79ded0f55
Source dataset
uspto-grants-1981_06
Patent number
US04272445

Reaction notes

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