Aluminium lithium hydride → HCID 15752757, compound

HRID 577181Notes

Reaction equation

HRID 577181 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15](OC)=[O:16])[CH3:8]>C1COCC1>[CH2:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[CH2:15][OH:16])[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59589393Methyl 3-ethylpyridine-4-carboxylate

Product 1

HCID 15752757HCID 15752757, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (956 mg, 5.8 mmol) was stirred in anhydrous THF (40 mL). A solution of methyl 3-ethylpyridine-4-carboxylate (904 mg, 3.97 mmol) in anhydrous THF (10 mL) was added at 0° C., and then stirred at room temperature for 1 hour. The reaction was quenched with an aqueous solution of sodium hydroxide and extracted 5 times with ethyl acetate. The organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, (3-ethylpyridin-4-yl)methanol was obtained as a yellow oil (770 mg, 97% 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 organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-3575dec201324732b28434895198194d
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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