Dimethyl Sulfoxide → HCID 54386541, compound

HRID 2397993Notes

Reaction equation

HRID 2397993 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][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][C@H:4]2[CH3:23].CS(C)=O.FC(F)(F)C(O)=O.C1(N=C=NC2CCCCC2)CCCCC1>C(OC(=O)C)C.N1C=CC=CC=1.C1C=CC=CC=1>[CH3:23][C@H:4]1[C@@:3]2([CH:2]=[O:1])[C:8]([CH2:9][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])=[CH:7][C:6](=[O:22])[CH2:5]1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 5427936919-Hydroxy-1beta-methyl-4-androsten-3,17-dione

Product 1

HCID 54386541HCID 54386541, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

19-Hydroxy-1β-methyl-4-androstene-3,17-dione is added to a mixture containing dimethylsulfoxide, benzene, pyridine, trifluoroacetic acid and N,N'-dicyclohexylcarbodiimide and allowed to react for 12 hours at room temperature. Ethylacetate is added and the reaction mixture is filtered. The filtrate is extracted with a solution of sodium bicarbonate, water and dried over magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue is crystallized from ether to yield 1β-methyl-4-androstene-3,17,19-trione.

Workup

  1. customto react for 12 hours at room temperature
  2. filtrationthe reaction mixture is filtered
  3. extractionThe filtrate is extracted with a solution of sodium bicarbonate, water
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent under reduced pressure
  6. customthe residue is crystallized from ether

Sources & evidence

ORD record
ord-fade28b16b224e2baf5485aca1c16618
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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