Pyridine → 19-(Triphenylsiloxy)-4-androstene-3,17-dione methanolate

HRID 371811

Reaction equation

HRID 371811 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>[CH3:2][O-: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 8673567919-(Triphenylsiloxy)-4-androstene-3,17-dione methanolate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 9.0 gm (0.03 mole) of 19-hydroxy-4-androstene-3,17-dione, 11.8 gm (0.04 mole) of triphenylchlorosilane and 9.6 gm (0.12 mole) of 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 recrystallized from methanol to yield 19-(triphenylsiloxy)-4-androstene-3,17-dione methanolate having a m.p. of 100°-2° C., uv max (MeOH) 223 nm (ε30,430), 242 nm (ε17,300).

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. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ae0960fedd104630aae6e0a71432e7d1
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Linked notes

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