Ethyl formate → Ethyl 2-(hydroxymethyl)-3-(3-pyridyl)butyrate

HRID 1855861Notes

Reaction equation

HRID 1855861 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH3:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:2]=1.[CH:15](OCC)=[O:16].[H-].[Na+]>C(COC)OC>[OH:16][CH2:15][CH:8]([CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 12727116Ethyl 3-(pyridin-3-yl)butanoate

Product 1

HCID 23349231Ethyl 2-(hydroxymethyl)-3-(3-pyridyl)butyrate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Treatment of ethyl 3-(3-pyridyl)butyrate with ethyl formate and sodium hydride in glyme, followed by acidification gave ethyl 2-(hydroxymethyl)-3-(3-pyridyl)butyrate, m.p. 128°-131°.

Sources & evidence

ORD record
ord-32ff5f353c454fb480eb0ec0fbe7b4c5
Source dataset
uspto-grants-1980_08
Patent number
US04216318

Reaction notes

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