Nitrogen → HCID 68295599, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-iodobenzoate (2.312 ml, 15.26 mmol), (2S)-3-butyne-1,2-diol (1.380 g, 16.03 mmol), and Et3N (10.64 ml, 76 mmol) in Acetonitrile (25.2 ml) was degassed with N2 for 10 min and treated with CuI (0.581 g, 3.05 mmol) and Pd(PPh3)4 (0.264 g, 0.229 mmol) and the reaction mixture was heated to 80° C. After 20 min, the reaction mixture was cooled to ambient temperature. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl, water and brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-100%) to afford the title compound (2.88 g, 13.08 mmol, 86% yield) as a beige solid: Rt=0.54 min, ES+ MS: 221 (M+1).

Provenance & Evidence