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

HRID 630236Notes

Reaction equation

HRID 630236 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[C:13]([C:14](OCC)=[O:15])=[C:12]([CH3:19])[CH:11]=[CH:10][N:9]=1>C1COCC1>[CH3:7][C:8]1[C:13]([CH2:14][OH:15])=[C:12]([CH3:19])[CH:11]=[CH:10][N:9]=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 8028TetrahydrofuranSolvent2×

Procedure

To the suspension of LAH (0.95 g, 25 mmol) in THF (100 mL), ethyl 2,4-dimethylpyridine-3-carboxylate (1.5 g, 8.4 mmol) was added dropwise as a solution in THF (10 mL) at 0° C. After 30 minutes, the reaction was quenched by addition of acetone/water and then more water (100 mL) was added. The mixture was extracted with DCM (3×100 mL), dried over magnesium sulfate, and evaporated to provide (2,4-dimethylpyridin-3-yl)methanol, which was used in the next step without any further purification.

Workup

  1. customthe reaction was quenched by addition of acetone/water
  2. additionmore water (100 mL) was added
  3. extractionThe mixture was extracted with DCM (3×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-1eafd1766a564d31be715b5c56c40d44
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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