Borane;tetrahydrofuran → [2-(Methylsulfanyl)pyridin-3-yl]methanol

Participants

Reaction Conditions

Reaction Steps

To 2-(methylthio)picolinic acid (1.00 g, 5.91 mmol) was added BH3.THF (1.0 M/THF, 15 mL, 15 mmol) and the mixture heated at 80° C. for 24 h. Methanol (30 mL) was carefully added at room temperature and the solution was concentrated in vacuo. Purification of the crude material on silica gel (20% EtOAc/hexanes) gave the title compound as colourless crystals (278 mg, 30%). 1H NMR (CDCl3) □ 1.99 (t, 1H, J=6.0 Hz), 2.61 (s, 3H), 4.70 (d, 2H, J=6.0 Hz), 7.04 (dd, 1H, J=6, 3 Hz), 7.62 (d, 1H, J=6 Hz), 8.40 (d, 1H, J=3 Hz).

Provenance & Evidence