Acetic Acid → 1-(Pyridin-2-yl)cyclobutane-1-carboxylic acid

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Reaction Steps

1-Pyridin-2-yl-cyclobutanecarbonitrile (4.92 g, 31.1 mmol) was combined with water (5 mL), AcOH (5 mL) and sulfuric acid (5 mL). The homogeneous solution was heated to reflux. After 2.5 h, the solution was cooled to room temperature and poured into water (20 mL) and Et2O. The layers were separated and the Et2O layer was discarded. The aqueous layer was basified to pH 4.5-5 with 10% NaOH and extracted with DCM (2×100 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to yield 3.28 g (59%) of 1-pyridin-2-yl-cyclobutanecarboxylic acid as pale yellow solid, m/z=178.5 [M+1]+.

Provenance & Evidence