Benzene → HCID 86736327, compound

HRID 1390786Notes

Reaction equation

HRID 1390786 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH:9]=[C:8]1[C@H:7]([CH3:22])[C:6](=[O:23])[CH2:5][C@@H:4]2[CH3:24].CS(C)=O.C1C=CC=CC=1.FC(F)(F)C(O)=O>C(OCC)(=O)C.N1C=CC=CC=1>[CH3:24][C@@H:4]1[C@@:3]2([CH:2]=[O:1])[C:8](=[CH:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[O:21])[C@H:7]([CH3:22])[C:6](=[O:23])[CH2:5]1

Participants

7

Reactant 4

HCID 241BenzeneHCID 679Dimethyl SulfoxideHCID 6422Trifluoroacetic acidHCID 7060533319-Hydroxy-1alpha,4alpha-dimethyl-5-androstene-3,17-dione

Product 1

HCID 86736327HCID 86736327, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

19-Hydroxy-1α,4α-dimethyl-5-androstene-3,17-dione is added to a mixture containing dimethylsulfoxide, benzene, pyridine, trifluoroacetic acid and N,N-dicyclohexylcarbodiimide and allowed to react for about 12 hours at room temperature. Ethyl acetate is added and the reaction mixture is filtered, extracted with a cold solution of sodium bicarbonate, washed with water, and dried over magnesium sulfate. After evaporation of the volatile solvents at room temperature under reduced pressure, the residue which remains is crystallized from an ether-pentane mixture to yield 1α,4α-dimethyl-5-androstene-3,17,19-trione.

Workup

  1. customto react for about 12 hours at room temperature
  2. filtrationthe reaction mixture is filtered
  3. extractionextracted with a cold solution of sodium bicarbonate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the volatile solvents at room temperature under reduced pressure
  7. customthe residue which remains is crystallized from an ether-pentane mixture

Sources & evidence

ORD record
ord-658f351b8e874762adbb8c5f50a4ab7c
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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