Triethylamine → 3-{3-[2-(5-Phenyl-furan-2-yl)-vinyl]-phenyl}-acrylic acid

Participants

Reaction Steps

To acid (28) (9.2 mg, 0.028 mmol) in DCM (1 mL), externally cooled to −78° C., was added methanesulphonyl chloride, (20 mg, 0.17 mmol) and triethylamine (29 mg, 0.29 mmol). The solution was then allowed to warm to ambient temperature and stirred for a further 2 hours. The solvent was concentrated in vacuo and the residue purified by Flash Master Jones Chromatography using a 2 g silica cartridge and eluting with 50% EtOAc in heptane to give the title compound as a white solid. Yield: 3.6 mg, 41%; LC-MS tr 1.77 min; NMR Purity: >85%; MS (ES+) m/z 317 (M+H); 1H NMR (400 MHz; DMSO): δ 6.70-6.80 (m, 2H), 7.15 (d, 1H), 7.25-7.35 (d, 1H), 7.35-7.45 (m, 2H), 7.50-7.60 (m, 4H), 7.65-7.75 (m, 3H), 7.90 (d, 2H), 8.10 (s, 1H)

Provenance & Evidence