Benzyl Alcohol → HCID 23535587, compound

Participants

Reaction Steps

To a suspension of 6-methylnicotinic acid (36.4 mmol) in toluene (100 mL) was added DIPEA (120 mmol) and Diphenylphosphoryl azide (91.1 mmol). The reaction mixture was heated to reflux for 1 h, cooled to RT and treated with benzyl alcohol (120 mmol). After 30 min ethyl acetate (200 mL) and water (200 mL) were added, the layers were separated and the organic layer washed with water (3×100 mL). The solvents were removed in vacuo and the residue was purified by preparative HPLC chromatography to give (6-methyl-pyridin-3-yl)-carbamic acid benzyl ester (5.2 g, 21.5 mmol, 59%) as a colourless oil.

Provenance & Evidence