Ethyl formate → HCID 20267148, compound

HRID 1719535Notes

Reaction equation

[H-].[Na+].[CH3:3][N:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]1=[O:17].[CH:18](OCC)=[O:19]>C(COC)OC>[CH:18]([CH:11]([CH2:10][C:7]1[CH:8]=[CH:9][N:4]([CH3:3])[C:5](=[O:17])[CH:6]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:19]

Participants

Conditions

Temperature: -5 °C

Procedure

To a stirred suspension of 57% sodium hydride in oil (6.55 g) in dimethoxyethane (40 ml) at -5° C., was added dropwise over 40 minutes a mixture of ethyl β-(N-methyl-2-oxo-4-pyridyl)propionate (26.05 g) and ethyl formate (13.83 g) whilst maintaining the reaction temperature at -5° C. The temperature of the reaction mixture was slowly allowed to rise to ambient at which temperature it was stood for three days. The reaction mixture was poured on to ice, extracted with diethyl ether (3×100 ml) and the combined organic layers were washed with water (2×20 ml). The aqueous layer and washings were acidified to pH 4 with 2 N sulphuric acid whereupon a solid came out of solution. The mixture was kept at 0° C. for two hours, and the solid filtered off and dried in vacuo to afford ethyl α-formyl-β-(N-methyl-2-oxo-4-pyridyl)propionate (15.27 g) as a solid; recrystallisation from isopropanol afforded a solid, m.p. 164-5-165.5 ° C.

Workup

additionwas added dropwise over 40 minutes
additionThe reaction mixture was poured on to ice
extractionextracted with diethyl ether (3×100 ml)
washthe combined organic layers were washed with water (2×20 ml)
waitThe mixture was kept at 0° C. for two hours
filtrationthe solid filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-f0025fca81ab4b968b6df7d22c1bfbb7
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04540699

Reaction notes

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