p-Toluenesulfonic acid → HCID 54014865, compound

HRID 1658707Notes

Reaction equation

HRID 1658707 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@:4]1([CH3:22])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:21])[CH2:6][CH2:5]1.C(O)(C)(C)C.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)CCl>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@:4]1([CH3:22])[C:9]([CH:10]=[CH:11]2)=[CH:8][C:7](=[O:21])[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6386tert-ButanolHCID 8371ChloranilHCID 13990933HCID 13990933, compound

Product 1

HCID 54014865HCID 54014865, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2.3 g. of 11β-fluoro-4-androstene-3,17-dione is stirred under reflux in 25 ml. of tert.-butanol and 15 ml. of ethylene chloride with 4 g. of chloranil and 50 mg. of p-toluenesulfonic acid for 6 hours. After the reaction mixture has been worked up as described in Example 16 and chromatographed on silica gel with acetone/hexane, 1.2 g. of 11β-fluoro-4,6-androstadiene-3,17-dione is obtained. UV: ε280 = 25,600.

Workup

  1. temperatureunder reflux in 25 ml
  2. customchromatographed on silica gel with acetone/hexane, 1.2 g

Sources & evidence

ORD record
ord-9cdedd9bb64b44d5af971646f99e71a0
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

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