Benzyl Alcohol → 6-Benzyloxy-2-picoline 1-oxide

Participants

Reaction Steps

0.80 g of 6-chloro-2-picoline 1-oxide was added to an alcoholate solution prepared from 0.33 g of 60% oily sodium hydride, 0.69 ml of benzyl alcohol and 5 ml of dimethyl sulfoxide. The mixture was stirred overnight at room temperature. 1N-HCl (1.7 ml) was added to the reaction mixture and then water and chloroform were added. The organic layer was separated, and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Wakogel C-200, 100 g; eluting solvent: chloroform/methanol=80/1→40/1) to give 0.64 g (yield 54%) of 6-benzyloxy-2-picoline 1-oxide.

Provenance & Evidence