Pyridine → 19-Trimethylsiloxy-4-androstene-3,17-dione

HRID 1390775Notes

Reaction equation

HRID 1390775 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][CH2:4]2.[CH3:23][Si:24]([CH3:27])([CH3:26])Cl.N1C=CC=CC=1>C1C=CC=CC=1>[CH3:23][Si:24]([CH3:27])([CH3:26])[O: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][CH2:4]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 25237919-Hydroxyandrostenedione

Product 1

HCID 2280149719-Trimethylsiloxy-4-androstene-3,17-dione

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 19-hydroxy-4-androstene-3,17-dione, trimethylchlorosilane and pyridine is refluxed in benzene for a period of 18 hours. The resulting suspension is filtered, the volatiles removed in vacuo and concentrated to a yellow oil. The oil is placed upon a silica gel chromatographic column packed in chloroform and eluted with chloroform. The chloroform eluate is evaporated to dryness in vacuo and the residue is recrystallized twice from hexane to yield the desired 19-(trimethylsiloxy)-4-androstene-3,17-dione.

Workup

  1. filtrationThe resulting suspension is filtered
  2. customthe volatiles removed in vacuo
  3. concentrationconcentrated to a yellow oil
  4. washeluted with chloroform
  5. customThe chloroform eluate is evaporated to dryness in vacuo
  6. customthe residue is recrystallized twice from hexane

Sources & evidence

ORD record
ord-dc3bce60d3ec46e392113a5860cba5b8
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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