Sodium methanethiolate → 2-Furanmethanethiol, 5-(3-pyridinyl)-

Participants

Reaction Steps

(See FIG. 7.) To a solution of 13 (10 mg, 0.05 mmol) in CHCl3/CH3OH (1.5 mL, 2:1, v:v) was added sodium thiomethoxide (3 mg, 0.05 mmol) and the resultant solution was stirred under argon for 10 min. The solvent was removed with a stream of argon and the residue was applied directly to a TLC plate (20×20 cm, 250 μm silica gel), developed (EtOAc/Hex, 5/95, Rf=0.12), the product band was scraped, extracted with dichloromethane and the solvent was removed in vacuo to afford the title compound 14 (6 mg, 68% yield) as a white film: 1H NMR (CD3OD) δ 8.72 (m, 1H), 8.19 (m, 1H), 7.96 (m, 1H), 7.28 (m, 1H), 6.66 (d, J=3.3 Hz, 1H), 6.07 (d, J=3.3 Hz, 1H), 3.59 (s, 2H), LRMS (ESI) m/z calcd for C10H10NOS [M+H]+ 192. found 192.

Provenance & Evidence