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

HRID 371810

Reaction equation

HRID 371810 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-dd803cd3723f47a39891acfd9ac3d996
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Linked notes

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