Water → 3-Methylandrost-5-en-17-one

HRID 1086255Notes

Reaction equation

HRID 1086255 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C@H:7]3[C@H:10]4[C@H:20]([CH2:21][CH2:22][C@:5]23[CH3:6])[C@:18]2([CH3:19])[C:13]([CH2:14][C@@H:15]([CH3:23])[CH2:16][CH2:17]2)=[CH:12][CH2:11]4)[O:3]C1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CC(C)=O>[CH3:23][C@H:15]1[CH2:16][CH2:17][C@@:18]2([CH3:19])[C:13](=[CH:12][CH2:11][C@@H:10]3[C@@H:20]2[CH2:21][CH2:22][C@@:5]2([CH3:6])[C@H:7]3[CH2:8][CH2:9][C:4]2=[O:3])[CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 18644451HCID 18644451, compound

Product 1

HCID 1289153-Methylandrost-5-en-17-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The 3β-methylandrost-5-en-17-one 17-ethylene ketal (13) (2.20 g 6.7 mmol) was dissolved in acetone (100 ml). p-Toluenesulfonic acid (100 mg) and H2O (20 ml) were added and the solution was refluxed for 2 hours. The solution was evaporated, taken up in ether (30 ml), washed with saturated NaHCO3, H2O, and then dried over MgSO4. The solution was filtered and evaporated to give a colorless solid which was recrystallized from methanol to give 3β-methylandrost-5-en-17-one (14) as colorless plates, 1.17 g (61%) mp 148°-150° C.; IR(KBr) 3010, 2910, 1740, 1455, 1430, 1365 cm-1 ; 1H NMR (CDCl3) δ5.41 (brd, J=6Hz, 1H, H-6), 1.11 (s, 3H, C-19 Me), 0.99 (s, 3H, C-18 Me), 1.07 (d, 3H, C-3 Me); MS (m/e) 286 (M+, 58), 271 (51), 229 (31), 159 (36), 105 (72), 9- (95), 79 (89), 55 (9), 41 (100).

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. customThe solution was evaporated
  3. washwashed with saturated NaHCO3, H2O
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. customevaporated
  7. customto give a colorless solid which
  8. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-01067f96de7a4e1f8f7c3de8d26216bc
Source dataset
uspto-grants-1991_07
Patent number
US05028631

Reaction notes

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