4-Nitrophenyl chloroformate → HCID 15382527, compound

Participants

Reaction Steps

A solution of benzofuran-2-ylmethanol 59 (300 mg, 2.03 mmol) in THF (5 mL) was cooled to 0° C. TEA (280 μL, 2.03 mmol) was added dropwise followed by the portionwise addition of p-nitrophenyl chloroformate (282 mg, 3.05 mmol). The resulting solution was stirred at room temperature for 2 h. Solvent was evaporated off in vacuo and the crude residue was purified by flash chromatography, eluting with hexane:EtOAc (3:1) to give 60 (350 mg, 54%) as a white solid. H1 NMR (500 MHz, CDCl3): δ=8.31 (2H, m, ArH), 7.62 (1H, d, J=7.70 Hz, ArH), 7.54 (1H, d, J=7.70 Hz, ArH), 7.43-7.27 (3H, m, ArH), 7.29 (1H, t, J=7.72 Hz, ArH), 6.93 (1H, s, ArH), 5.43 (2H, s, CH2). 13C NMR CDEPT 135, (500 MHz, CDCl3): δ=125.47, 125.37, 123.23, 121.80, 121.66, 111.60, 108.53, 62.95.

Provenance & Evidence