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

HRID 1733069Notes

Reaction equation

HRID 1733069 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 9.0 gm (0.03 mole) of 19-hydroxy-4-androstene-3,17-dione, 4.3 gm (0.04 mole) of trimethylchlorosilane and 3.2 gm (0.04 mole) of pyridine is refluxed in 100 ml of 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 having a m.p. of 87°-9° C., uv max (MeOH) 242 nm (ε14,700).

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-8ae1ea4366b2467abd7ee08d35d75ae3
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

Loading…