p-Toluenesulfonic acid → HCID 70464278, compound

HRID 2199082Notes

Reaction equation

HRID 2199082 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(O)(=O)C.C(OC(=O)C)(=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 88.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 9-fluoro-11β-hydroxyandrosta-1,4-diene-3,17-dione (5.0 g) in a mixture of acetic acid (60 ml) and acetic anhydride (60 ml) containing p-toluenesulfonic acid (2.5 g) is maintained at room temperature for eighteen hours. Sodium acetate (2.5 g) is added and the mixture is concentrated in vacuo at 35°-40° C. The residue is diluted with water (150 ml) and the solid that separates is isolated by filtration, washed with water and dried in vacuo to afford the title compound as a solid (5.0 g) with consistent spectral data. An examination (silica gel, chloroform: ethyl acetate, 95:5) reveals the presence of a small amount of starting steroid as the only significant impurity. This material is used without purification in the next step. A specimen crystallized from acetone-hexane melts at 173°-174° C.

Workup

  1. concentrationthe mixture is concentrated in vacuo at 35°-40° C
  2. additionThe residue is diluted with water (150 ml)
  3. customthe solid that separates is isolated by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-13a9bb9088704e3e8cfda21da5780cf1
Source dataset
uspto-grants-1982_11
Patent number
US04361559

Reaction notes

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