Benzene → Methyl 5-isopropoxynicotinate

Participants

Reaction Conditions

Reaction Steps

A solution of 677 mg (3.28 mmol) of dicyclohexylcarbodiimide (DCC), 0.3 mL (3.92 mmol) of isopropanol, and 7.7 mg (0.078 mmol) of CuCl was heated at 60° C. After 13 h, 460 mg (3.0 mmol) of 5-hydroxynicotinic acid methyl ester and 10 mL of benzene were added and heated at 105° C. for 24.5 h. The mixture was diluted with chloroform and filtered. The organic layer was washed with 15 mL of sat. NaHCO3, water, and brine and dried over Na2SO4. Purification by flash silica gel chromatography (100% CHCl3) provided 274 mg of methyl 5-isopropoxynicotinate as a yellow oil in 47% yield.

Provenance & Evidence