Reaction #7264

Reaction equation

2-Methylnicotinic acid

BH3.THF

→

alcohol

Yield 80.0%

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

Yield 80.0%

Solvents

MeOH

Conditions

Workup

1. 1
   Temperaturebefore being cooled to room temperature
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe resultant crude syrup was repeatedly dissolved in MeOH (5 mL)
4. 4
   Concentrationconcentrated (3×)
5. 5
   OtherPurification by column chromatography on silica gel (4:1—EtOAc:Hexanes)

Procedure

To 2-Methylnicotinic acid (1.00 g, 7.29 mmol) was added BH3.THF (1.0 m in THF, 18 mL, 18 mmol) and the resultant mixture was heated to 80° C. for 20 hours. MeOH (6 mL) was added and the mixture was heated to 80° C. for an additional 2 hours before being cooled to room temperature and concentrated under reduced pressure. The resultant crude syrup was repeatedly dissolved in MeOH (5 mL) and concentrated (3×). Purification by column chromatography on silica gel (4:1—EtOAc:Hexanes) afforded the desired alcohol (700 mg, 80%) as a white solid. 1H NMR (CDCl3) δ 1.96 (t, 1H, J=5.4 Hz), 2.73 (s, 3H), 4.81 (d, 2H, J=5.4 Hz), 7.32 (dd, 1H, J=7.8, 6.3 Hz), 8.03 (d, 1H, J=7.8 Hz), 8.73 (d, 1H, J=5.7 Hz).

Source