Triethylamine → HCID 10374617, compound

Participants

Reaction Steps

To a solution of 4-pentynoic acid (981 mg, 10 mmol) in THF (40 mL) and DMF (2 drops) was added dropwise oxalyl chloride (0.96 mL, 11 mmol) over 10 min. The solution was stirred for 3 h at rt, then the flask was cooled in an ice bath and a solution of pyrrolidine (1.65 mL, 20 mmol) and Et3N (1.74 mL, 12.5 mmol) in THF (10 mL) was added dropwise over 17 min. The resulting suspension was stirred overnight, then filtered. The filtrate was partitioned between EtOAc (300 mL) and H2O. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated to dryness, giving the desired product as a brown solid (1.32 g, 87%). MS (APCI(+)) m/e 152.1 (M+H)+.

Provenance & Evidence