HCID 70538349, compound → HCID 56627596, compound

HRID 1578021Notes

Reaction equation

HRID 1578021 reaction equation
C(O[C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C@@H:23]([O:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:37])[C@@H:18]4[CH2:36][C@@H:19]42)[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[C:6](=[O:8])[CH3:7])(=O)C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[C:28]([O:27][C@H:23]1[CH2:24][C@@:25]2([CH3:26])[C@@H:11]([CH2:10][CH:9]=[C:5]2[C:6](=[O:8])[CH3:7])[C@H:12]2[C@H:22]1[C@:20]1([CH3:21])[C:15]([CH:14]=[CH:13]2)=[CH:16][C:17](=[O:37])[C@@H:18]2[CH2:36][C@H:19]12)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 1

HCID 70538349HCID 70538349, compound

Product 1

HCID 56627596HCID 56627596, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

One gram of 17α-acetoxy-11β-benzoyloxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione is dissolved in 10 ml of "Dowtherm" (filtered over A12O3). The solution is heated under a stream of nitrogen gas for 30 minutes to 285° C. After cooling, the mixture is diluted with hexane, introduced into a silica gel column, and the "Dowtherm" is eluted with hexane. The thus-prepared compound is now eluted with methylene chloride and a gradually increasing proportion of chloroform. The individual fractions are tested for content and purity by thin-layer chromatography. The fractions having the desired compound are combined, concentrated, and the residue is recrystallized from benzene, thus obtaining 700 mg of 11β-benzoyloxy-1α,2α-methylene-4,6,16-pregnatriene-3,20-dione (79% of theory), m.p. 227°-229° C.

Workup

  1. filtrationfiltered over A12O3)
  2. temperatureThe solution is heated under a stream of nitrogen gas for 30 minutes to 285° C
  3. temperatureAfter cooling
  4. additionthe mixture is diluted with hexane
  5. additionintroduced into a silica gel column
  6. washthe "Dowtherm" is eluted with hexane
  7. washThe thus-prepared compound is now eluted with methylene chloride
  8. temperaturea gradually increasing proportion of chloroform
  9. concentrationconcentrated
  10. customthe residue is recrystallized from benzene

Sources & evidence

ORD record
ord-3f3edbe8a0754d5b9d1ae63a6bac06f6
Source dataset
uspto-grants-1981_09
Patent number
US04290963

Reaction notes

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