1,2-Dichloroethane → HCID 70626772, compound

HRID 616349Notes

Reaction equation

HRID 616349 reaction equation
[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C@@H:23]([F:27])[CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:28])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].C(Cl)CCl.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)(C)C>[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C@@H:23]([F:27])[CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:28])[CH2:18][CH2:19]2)[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6101p-Toluenesulfonic acidHCID 8371ChloranilHCID 70626160HCID 70626160, compound

Product 1

HCID 70626772HCID 70626772, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

One gram of 17-acetoxy-11β-fluoro-4-pregnene-3,20-dione is combined in a solvent mixture of 6 ml. of ethylene chloride and 10 ml. of tert.-butanol with 1.5 g. of chloranil and 10 mg. of p-toluenesulfonic acid. The mixture is heated for 6 hours under reflux. Then, the mixture is filtered off from the chloranil and the precipitate washed with ethyl acetate and ether. The filtrate is diluted with ether and combined repeatedly with 2N NaOH solution. The solution is then washed neutral with water and dried. After chromatography of the crude product on silica gel with 14- 17% acetone/hexane, 344 mg. of 17-acetoxy-11β-fluoro-4,6-pregnadiene-3,20-dione is obtained; m.p. 220°-222° C. from acetone/hexane. UV: ε280 = 26,500.

Workup

  1. temperatureThe mixture is heated for 6 hours
  2. temperatureunder reflux
  3. filtrationThen, the mixture is filtered off from the chloranil
  4. washthe precipitate washed with ethyl acetate and ether
  5. additionThe filtrate is diluted with ether
  6. washThe solution is then washed neutral with water
  7. customdried

Sources & evidence

ORD record
ord-caa72e3468fb490abd01eef4068c48ea
Source dataset
uspto-grants-1978_02
Patent number
US04073900

Reaction notes

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