4-Pyridineethanol → 4-(2-Hydroxyethyl)pyridine-2-carbonitrile

HRID 1164868Notes

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.OCCC1C=C[N+:16]([O-])=[CH:15]C=1.C[Si](C#N)(C)C>>[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:15]#[N:16])[CH:5]=1

Participants

Reactant 3

HCID 729214-Pyridineethanol

HCID 82115Trimethylsilyl cyanide

HCID 197578414-(2-hydroxyethyl)-pyridine-N-oxide

Product 1

HCID 223216614-(2-Hydroxyethyl)pyridine-2-carbonitrile

Procedure

4-(2-hydroxyethyl)-pyridine is oxidized to 4-(2-hydroxyethyl)-pyridine-N-oxide which is in turn treated with trimethylsilyl cyanide to yield 4-(2-hydroxyethyl)-2-cyanopyridine which is converted to ethyl 4-(2-hydroxyethyl)-2-pyridine carboxylate and then hydrogenated to yield ethyl 4-(2-hydroxyethyl)-piperidine-2-carboxylate.

Sources & evidence

ORD record: ord-9b0fb40e0a0844138666f79d36eb847e
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04906621

Reaction notes

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