Synthesis
Add lithium aluminum hydride (1.0M in THF; 1.5mL, 1.5mmol, 0.5equiv) over a period of 3 min to a solution of 5-cyano-nicotinic acid methyl ester (479mg, 2.95mmol, 1 equiv) in anhydr THF (15mL) and cool to -78°C After 1h while still at -78°C, quench the reaction with H2O (60μL), 5M aq NaOH (60μL), and more H2O (180μL). Filter the reaction mixture through paper. Rotary evaporate the filtrate (40°C) to give 369mg of material as a yellow solid. Transfer this material to a column of silica gel (130mm x 25mmdia.) and elute (2% MeOH/CH2Cl2) to yield 180mg of a mixture of ester, hemiacetal, and aldehyde as a yellow solid and 45mg (11%) of 5-hydroxymethyl-nicotinonitrile as a yellow solid. MS (m/e): 163.07 (M+1).
