Reaction #7247

Reaction equation

3-ethoxypicolinic acid

BH3.THF

→

alcohol

Yield 124.6%

3-ethoxy-2-hydroxymethylpyridine

Yield 124.6%

Solvents

THF

Conditions

Workup

1. 1
   OtherThe mixture was then quenched with methanol (20 mL)
2. 2
   workup.STIRRINGstirred
3. 3
   Temperatureat reflux for 4 hours
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe resultant crude product was dissolved in methanol (3×15 mL)
6. 6
   Concentrationconcentrated

Procedure

To a solution of 3-ethoxypicolinic acid (0.202 g, 1.21 mmol) in dry THF (1 mL) was added BH3.THF (1.0 M in THF, 5.0 mL, 5.0 mmol) and the reaction mixture stirred at room temperature for 2.5 hours. The mixture was then quenched with methanol (20 mL), stirred at reflux for 4 hours and concentrated under reduced pressure. The resultant crude product was dissolved in methanol (3×15 mL) and concentrated to give the desired crude alcohol (0.231 g) as an orange solid. 1H NMR (CDCl3): δ 1.46 (t, 3H, J=7.0 Hz), 4.07 (q, 2H, J=7.0 Hz), 4.74 (s, 2H), 7.09–7.20 (m, 2H), 8.14 (d, 1H, J=4.5 Hz).

Source