p-Toluenesulfonic acid → HCID 70464278, compound

HRID 839470Notes

Reaction equation

HRID 839470 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.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:35]([O-])(=[O:37])[CH3:36].[Na+]>C(OC(=O)C)(=O)C.C(O)(=O)C>[C:35]([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:37])[CH3:36]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 517045Sodium AcetateHCID 13421116HCID 13421116, compound

Product 1

HCID 70464278HCID 70464278, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 9-fluoro-11β-hydroxyandrosta-1,4-diene-3,17-dione (2.0 g) in a mixture of acetic anhydride (20 ml) and acetic acid (10 ml) containing p-toluenesulfonic acid (200 mg) is kept at room temperature for 40 hours. Sodium acetate (1.0 g) is added and the mixture is evaporated in vacuo. The residue is diluted with water and extracted with chloroform. The chloroform extracts are combined, washed with a dilute sodium bicarbonate solution and water, dried, evaporated and the residue is chromatographed on a column of silica gel to afford the title compound (1.6 g), melting point 229°-230° C.

Workup

  1. customthe mixture is evaporated in vacuo
  2. additionThe residue is diluted with water
  3. extractionextracted with chloroform
  4. washwashed with a dilute sodium bicarbonate solution and water
  5. customdried
  6. customevaporated
  7. customthe residue is chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-5303fca9da7643bdb81b999a2c24def7
Source dataset
uspto-grants-1978_06
Patent number
US04094840

Reaction notes

Loading…