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

HRID 1390776Notes

Reaction equation

HRID 1390776 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.[C:23]1([Si:29]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)Cl)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1C=CC=CC=1>C1C=CC=CC=1>[C:37]1([Si:29]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:1][CH2:2][C@@:3]23[C@@H:20]4[C@H:11]([C@H:12]5[C@@:16]([CH2:18][CH2:19]4)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]5)[CH2:10][CH2:9][C:8]2=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]3)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 25237919-Hydroxyandrostenedione

Product 1

HCID 2280323919-Triphenylsiloxy-4-androstene-3,17-dione

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 19-hydroxy-4-androstene-3,17-dione, triphenylchlorosilane and pyridine contained in 100 ml of benzene is refluxed for a period of 18 hours. The resulting suspension is filtered and concentrated in vacuo to a yellow oil. The oil is placed on a silica gel chromatographic column packed in chloroform which is further eluted with chloroform. The chloroform eluant is evaporated to dryness in vacuo and the residue is recrystallized from methanol to yield 19-triphenylsiloxy-4-androstene-3,17-dione.

Workup

  1. temperatureis refluxed for a period of 18 hours
  2. filtrationThe resulting suspension is filtered
  3. concentrationconcentrated in vacuo to a yellow oil
  4. washis further eluted with chloroform
  5. customThe chloroform eluant is evaporated to dryness in vacuo
  6. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-be551a2cf23b40c58c124028ed6ac0a6
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

Loading…