Pyridine → HCID 22797479, compound

HRID 2398007Notes

Reaction equation

HRID 2398007 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:25]([CH2:26][CH2:27][C@:6]12[CH3:7])[C@:19]1([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C:14](=[CH:15][C@@H:16]([OH:28])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2].[CH3:29][Si:30]([CH3:33])([CH3:32])Cl.N1C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:25]([CH2:26][CH2:27][C@:6]12[CH3:7])[C@:19]1([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C:14](=[CH:15][C@@H:16]([O:28][Si:30]([CH3:33])([CH3:32])[CH3:29])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 70585967HCID 70585967, compound

Product 1

HCID 22797479HCID 22797479, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-androstene-3β,17β,19-triol 17,19-diacetate, trimethylchlorosilane and pyridine in toluene is refluxed for 24 hours. The solid is removed by filtration and the filtrate reduced to dryness under vacuum. The oil is crystallized from hexane to yield 3β-trimethylsiloxy-4-androstene-17β,19-diol 17,19-diacetate. This produce is refluxed one hour with 1 equivalent of sodium bicarbonate in 10% aqueous methanol. The solution is poured onto water. The solid which forms is filtered, dried, and crystallized from ether-hexane to yield 3β-trimethylsiloxy-4-androstene-17β,19-diol 17-acetate.

Workup

  1. customThe solid is removed by filtration
  2. customThe oil is crystallized from hexane

Sources & evidence

ORD record
ord-333eeefe38124a80b4fe9b1219e6b0bf
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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