Methyl 6-methylnicotinate → (6-Methylpyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

In a 500 ml round-bottomed flask at room temperature under nitrogen, methyl 6-methyl-3-pyridinecarboxylate (10 g, 66.2 mmol) was dissolved in dry tetrahydrofuran (100 ml) to give a orange solution. The mixture was then cooled down to 0° C. and lithium aluminum hydride (36.4 ml, 72.8 mmol) was added dropwise, keeping internal temperature below 0° C. At the end of addition the ice-bath was removed and the resulting solution was stirred at room temperature for 3 hours. The mixture was slowly additioned with 2.73 ml of water, 2.73 ml of NaOH 1M and 8.2 ml of water. The resulting yellow suspension was stirred at room temperature for ˜30 minutes and then filtered over a Gooch funnel. The solid was washed with Et2O (3×100 ml). The combined organics were dried over Na2SO4, filtered and concentrated to give the title product (7.48 g) as orange oil.

Provenance & Evidence