p-Toluenesulfonic acid → HCID 70464278, compound

HRID 2199085Notes

Reaction equation

HRID 2199085 reaction equation
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:21])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH:4]=[CH:5][C:6](=[O:22])[CH:7]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[C:24]([O:20][C@H:19]1[CH2:18][C@@:16]2([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]2=[O:21])[C@H:11]2[C@@:2]1([F:1])[C@:3]1([CH3:23])[C:8]([CH2:9][CH2:10]2)=[CH:7][C:6](=[O:22])[CH:5]=[CH:4]1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 13421116HCID 13421116, compound

Product 1

HCID 70464278HCID 70464278, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 20 g of 9-fluoro-11β-hydroxyandrosta-1,4-diene-3,17-dione, 120 ml of glacial acetic acid, 120 ml of acetic anhydride and 5 g of p-toluenesulfonic acid is stirred at room temperature under nitrogen for 24 hours. The resulting solution is quenched with 5 g of sodium acetate. The solvent is partially removed in vacuo at 35°-40° C. and the resultant slurry is diluted with chloroform. The chloroform solution is washed with water, saturated sodium bicarbonate and water, dried over anhydrous Na2SO4 and evaporated in vacuo to give the title compound. This is crystallized from ethyl acetate-hexane to give 20 g of the title compound melting point 171°-174° C., with consistent spectral data.

Workup

  1. customThe resulting solution is quenched with 5 g of sodium acetate
  2. customThe solvent is partially removed in vacuo at 35°-40° C.
  3. additionthe resultant slurry is diluted with chloroform
  4. washThe chloroform solution is washed with water, saturated sodium bicarbonate and water
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8f36a6ffc6a84c99a2dd12b79690a044
Source dataset
uspto-grants-1982_11
Patent number
US04361559

Reaction notes

Loading…