Malonic Acid → Ethyl 2-formyl-3-(2-methoxy-4-pyridyl)propionate

HRID 1248296Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=O)[CH:6]=[CH:5][N:4]=1.[C:11]([OH:17])(=[O:16])[CH2:12][C:13]([OH:15])=O.C(O[CH2:21][CH3:22])=O.[H-].[Na+]>>[CH:13]([CH:12]([CH2:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=1)[C:11]([O:17][CH2:21][CH3:22])=[O:16])=[O:15]

Participants

Reactant 4

HCID 867Malonic Acid

HCID 8025Ethyl formate

HCID 24758Sodium hydride

HCID 27629962-Methoxypyridine-4-carbaldehyde

Product 1

HCID 21273312Ethyl 2-formyl-3-(2-methoxy-4-pyridyl)propionate

Procedure

Condensation of 2-methoxypyridine-4-carboxaldehyde with malonic acid with subsequent esterification and hydrogenation at 344 kPa and formylation of the product with ethyl formate and sodium hydride gave ethyl 2-formyl-3-(2-methoxy-4-pyridyl)propionate as an oil.

Sources & evidence

ORD record: ord-0e86dbfcedaf4bf6bccdb9ca050acb87
Source dataset: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04523015

Reaction notes

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