Reaction #7263

Reaction equation

2-Hydroxynicotinic acid

BH3.THF

MeOH

→

alcohol

Yield 29.0%

3-hydroxymethyl-pyridin-2-ol

Yield 29.0%

Solvents

THF

Conditions

Workup

1. 1
   Temperaturethe mixture was heated to 80° C. for an additional 2 hours
2. 2
   Temperaturebefore being cooled to room temperature
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe resultant crude syrup was repeatedly dissolved in MeOH (5 mL)
5. 5
   Concentrationconcentrated (3×)
6. 6
   OtherPurification by column chromatography on silica gel (20:1—CH2Cl2: MeOH)

Procedure

To a suspension of 2-Hydroxynicotinic acid (1.01 g, 7.26 mmol) in THF (2 mL) was added BH3.THF (1.0 m in THF, 18 mL, 18 mmol) and the mixture was heated to 80° C. for 18 hours. MeOH (2 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 (20:1—CH2Cl2: MeOH) afforded the desired alcohol (260 mg, 29%) as a white solid. 1H NMR (CD3OD) δ 4.50 (s, 2H), 6.43 (t, 1H, J=6.6 Hz), 7.34 (d, 1H, J=4.5 Hz), 7.65 (d, 1H, J=6.3 Hz).

Source