Reaction #7258

Reaction equation

2-(methylthio)picolinic acid

BH3.THF

→

title compound

Yield 30.3%

(2-methylsulfanyl-pyridin-3-yl)-methanol

Yield 30.3%

Solvents

Methanol

Conditions

Workup

1. 1
   Concentrationthe solution was concentrated in vacuo
2. 2
   OtherPurification of the crude material on silica gel (20% EtOAc/hexanes)

Procedure

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).

Source