Pyridine → 1alpha-Methyl-17beta-trimethylsiloxy-4-androsten-19-one

HRID 2397981Notes

Reaction equation

HRID 2397981 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH:17]=[O:18])[C:11](=[CH:12][CH2:13][CH2:14][C@@H:15]1[CH3:22])[CH2:10][CH2:9]3.[CH3:23][Si:24]([CH3:27])([CH3:26])Cl.N1C=CC=CC=1>C1C=CC=CC=1>[CH3:22][C@@H:15]1[C@@:16]2([CH:17]=[O:18])[C:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:19]2[CH2:20][CH2:21][C@@:3]2([CH3:4])[C@H:5]3[CH2:6][CH2:7][C@@H:2]2[O:1][Si:24]([CH3:27])([CH3:26])[CH3:23])=[CH:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 8673473617beta-Hydroxy-1alpha-methyl-4-androsten-19-one

Product 1

HCID 227974621alpha-Methyl-17beta-trimethylsiloxy-4-androsten-19-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 17β-hydroxy-1α-methyl-4-androsten-19-one, trimethylchlorosilane and pyridine is refluxed in benzene for a period of about 18 hours. The suspension is filtered and the benzene removed under vacuum. The resulting oil is eluted from a silica gel chromatograph with benzene and crystallized from hexane to yield 1α-methyl-17β-trimethylsiloxy-4-androsten-19-one.

Workup

  1. filtrationThe suspension is filtered
  2. customthe benzene removed under vacuum
  3. washThe resulting oil is eluted from a silica gel chromatograph with benzene
  4. customcrystallized from hexane

Sources & evidence

ORD record
ord-48c98a8e1e484003ad2460da471f252f
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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