Ethyl propiolate → HCID 18358858, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl propiolate (4.05 mL, 40 mmol) in tetrahydrofuran (125 mL) at −78° C. under nitrogen was added n-BuLi (2.5 mL, 40 mmol, 1.6 M in hexane). The reaction mixture was stirred at about −70° C. for 0.5 hours and then 2-nitro-5-chlorobenzaldehyde (6.75 g, 36.4 mmol) was added dropwise. The reaction mixture was stirred at 78° C. for 0.25 hours, warmed to −60° C., quenched with acetic acid (5 mL) and then warmed to room temperature. The reaction mixture was partitioned between ether (250 mL) and water (250 mL). The layers were separated and the organic layer was washed with brine (250 mL) and dried over Na2SO4. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (4:1) to afford 6.12 g (59%) of the title compound as a yellow oil which solidified on standing.

Provenance & Evidence