Aluminium lithium hydride → HCID 66815231, compound

HRID 577138Notes

Reaction equation

HRID 577138 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[C:9]=1[C:17]([O-])=[O:18]>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[C:9]=1[CH2:17][OH:18]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86647909HCID 86647909, compound

Product 1

HCID 66815231HCID 66815231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (226 mg, 5.96 mmol) was stirred in anhydrous THF (30 mL). A solution of 4-chloro-2-(propan-2-yl)pyridine-3-carboxylate (904 mg, 3.97 mmol) in anhydrous THF (5 mL) was added at 0° C., and the reaction mixture was stirred at room temperature for 3 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, [4-chloro-2-(propan-2-yl)pyridin-3-yl]methanol was obtained as an oil (735 mg, 100% 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-913ebdfe60654b5aad573e8b4efb0da6
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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