Aluminium lithium hydride → (2-Ethylpyridin-3-yl)methanol

HRID 1685Notes

Reaction equation

HRID 1685 reaction equation
[Li+].[CH2:2]([C:4]1[N:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([O-])=[O:7])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:2]([C:4]1[C:5]([CH2:6][OH:7])=[CH:9][CH:10]=[CH:11][N:12]=1)[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 1317205572-Ethyl nicotinic acid lithium salt

Product 1

HCID 19690951(2-Ethylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. temperaturethen cooled to 0° C.
  2. customquenched with EtOAc (949 μL)
  3. filtrationThe solution was filtered
  4. customthe solvent removed under reduced pressure
  5. additionToluene was added
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-aaa0ddfbf41e452299afe064a36ec3cd
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Reaction notes

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