Ethyl 2,4-dimethylnicotinate → 2,4-Dimethyl-3-pyridinemethanol

HRID 1691Notes

Reaction equation

HRID 1691 reaction equation
[CH3:1][C:2]1[C:7]([C:8](OCC)=[O:9])=[C:6]([CH3:13])[CH:5]=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([CH3:13])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 736245Ethyl 2,4-dimethylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 103293512,4-Dimethyl-3-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 2,4-dimethyl-3-carboethoxypyridine (11.3 g, 63.1 mmol) in distilled THF (375 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF, 63.1 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0° C. and quenched with EtOAc (2.5 mL), then H2O (2.5 mL), then 15% NaOH (2.5 mL), followed by H2O (7.5 mL). The solution was filtered and the solvent removed under reduced pressure to give the desired 2,4-dimethyl-3-hydroxymethylpyridine.

Workup

  1. temperaturethen cooled to 0° C.
  2. customquenched with EtOAc (2.5 mL)
  3. filtrationThe solution was filtered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4b7921c79135478487a5a927dd9e4a45
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Reaction notes

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