Reaction #1781

Reaction equation

2-ethyl nicotinic acid lithium salt

lithium aluminum hydride

→

2-ethyl-3 -hydroxymethylpyridine

Solvents

THF

Conditions

Workup

1. 1
   Temperaturethen cooled to 0° C.
2. 2
   Otherquenched with EtOAc (949 μL)
3. 3
   FiltrationThe solution was filtered
4. 4
   Otherthe solvent removed under reduced pressure
5. 5
   workup.ADDITIONToluene was added
6. 6
   Otherthe solvent was removed under reduced pressure

Procedure

The 2-ethyl nicotinic acid lithium salt (5 g, 3.18 mmol) in distilled THF (400 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF) (25 mL) was added dropwise. The reaction was stirred for 3 hours at room temperature then cooled to 0° C. and quenched with EtOAc (949 μL), then H2O (949 μL), then 15% NaOH (949 μL), followed by H2O (2.8 mL). The solution was filtered and the solvent removed under reduced pressure. Toluene was added and the solvent was removed under reduced pressure to give the desired 2-ethyl-3 -hydroxymethylpyridine.

Source