Methanol → HCID 11324268, compound

Participants

Reaction Steps

3-[2-(1-phenylcyclopropyl)-1,3-thiazol-4-yl]benzonitrile (1-10, 0.10 g, 0.33 mmol) in MeOH (20 mL) was treated with NiCl2-6H2O (0.24 g, 1.0 mmol) and Zn metal (0.17 g, 2.6 mmol) and the resulting mixture was stirred vigorously at reflux for 72 h. The reaction was filtered through celite, concentrated, and partitioned between EtOAc (100 mL) and H2O (100 mL). The organic layer was concentrated and the crude residue was purified by reverse phase HPLC (C-8, 5-95% MeOH—H2O w/0.1% TFA) to provide pure {3-[2-(1-phenylcyclopropyl)-1,3-thiazol-4-yl]phenyl}methanol (5-1): 1H NMR (300 MHz, CDCl3) δ 7.82 (s, 1H), 7.79 (d, J=7.6 Hz, 1H), 7.52 (dt, J=6.8, 1.3 Hz, 2H), 7.40-7.30 (m, 5H), 7.32 (s, 1H), 4.76 (s, 2H), 1.87 (dd, J=6.8, 3.9 Hz, 2H), 1.44 (dd, J=6.8, 3.9 Hz, 2H); MS 307.9 found 309.4 (M+H+) required.

Provenance & Evidence