Aluminium lithium hydride → (2,4-Diethylpyridin-3-yl)methanol

HRID 577150Notes

Reaction equation

HRID 577150 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[C:14]([C:15](OCC)=[O:16])=[C:13]([CH2:20][CH3:21])[CH:12]=[CH:11][N:10]=1)[CH3:8]>C1COCC1>[CH2:7]([C:9]1[C:14]([CH2:15][OH:16])=[C:13]([CH2:20][CH3:21])[CH:12]=[CH:11][N:10]=1)[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59589505Ethyl 2,4-diethylpyridine-3-carboxylate

Product 1

HCID 59589353(2,4-Diethylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (410 mg, 10.8 mmol) was stirred in anhydrous THF (45 mL). A solution of ethyl 2,4-diethylpyridine-3-carboxylate (1.50 g, 7.2 mmol) in anhydrous THF (10 mL) was added at 0° C., and then stirred at room temperature for 2 hours. The reaction was quenched with an aqueous solution of sodium hydroxide and extracted 5 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, (2,4-diethylpyridin-3-yl)methanol was obtained as an oil (1.17 g, 98% yield) and used in the next step without further purification.

Workup

  1. customThe reaction was quenched with an aqueous solution of sodium hydroxide
  2. extractionextracted 5 times with ethyl acetate
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-f24ececc1cb34feb8164d0464731cbbd
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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