Oxalyl chloride → Ethyl 5-(3,4-difluorobenzyl)-1,2,4-oxadiazole-3-carboxylate

Participants

Reaction Steps

This compound was prepared according to general method 2 with (step I) 2-(3,4-difluorophenyl)acetic acid (0.651 g; 3.78 mmol) and oxalyl chloride (0.352 mL; 4.16 mmol) in dichloromethane (8 mL) with few drops of DMF and (step II) ethyl 2-amino-2-(hydroxyimino)acetate (0.5 g; 3.78 mmol) and N,N diisopropylethylamine (1.05 mL; 6.06 mmol) in dichloromethane (10 mL), and (step III) pyridine (18 mL). The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.346 g (34%) of ethyl 5-(3,4-difluorobenzyl)-1,2,4-oxadiazole-3-carboxylate as a yellow solid.

Provenance & Evidence