Benzyl mercaptan → HCID 59192525, compound

Participants

Reaction Steps

A solution of phenyl-methanethiol (0.8 mL, 5.84 mmol) in DMF (5 mL) was treated with NaH (0.140 g, 5.84 mmol) at room temperature under argon. After 15 min of stirring, the reaction mixture was treated with a solution of 2-chloro-5-(3-isopropyl-phenyl)-pyridine (0.900 g, 3.90 mmol) in DMF (15 mL). After 2 h of additional stirring at room temperature (reaction was monitored by TLC), the reaction mixture was quenched with ice cold water (20 mL), and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (2×10 mL), dried over Na2SO4, and concentrated in vacuo to obtain a crude product, which was purified over silica gel (Biotage column chromatography, gradient elution using 0-1% ethyl acetate in hexane) to furnish 2-benzylsulfanyl-5-(3-isopropyl-phenyl)-pyridine (0.680 g, 54.71%).

Provenance & Evidence