Triethylamine → HCID 58074949, compound

Participants

Reaction Conditions

Reaction Steps

5-Chloropyrazine-2-carboxylic acid (Intermediate 44, 21 g, 0.132 mol) was taken in thionyl chloride (100 mL) which was heated to reflux for 2 h and excess thionyl chloride was distilled off under reduced pressure to obtain a residue, which was dissolved in dry tetrahydrofuran (100 mL). In another round bottom flask ethyl hydrogen malonoate (15.8 g, 0.132 mol) was dissolved in tetrahydrofuran (500 mL) which was cooled to 0° C. To the resulting solution was added methyl magnesium bromide (88 mL, 0.265 M) and stirred the reaction mixture was stirred for 30 min before triethylamine (39.9 g, 0.396 M) was added. To this reaction mixture the above prepared acid chloride mixture was added, stirred for 2 h at room temperature and tetrahydrofuran was evaporated from the reaction mixture and the water (500 mL) was added and extracted with ethyl acetate (2×200 mL). The organic layers were combined and dried over anhydrous sodium sulphate, concentrated under reduced pressure to get obtain crude product which was purified by flash column chromatography (10% ethyl acetate/pet ether) to afford 16.0 g (53.16%) of ethyl 3-(5-chloropyrazin-2-yl)-3-oxopropanoate white solid.

Provenance & Evidence