Ethyl 4-chloro-2-ethylpyridine-3-carboxylate → (4-Chloro-2-ethylpyridin-3-yl)methanol

HRID 577146Notes

Reaction equation

HRID 577146 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][CH3:15])[C:9]=1[C:16](OCC)=[O:17]>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][CH3:15])[C:9]=1[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 19902853Ethyl 4-chloro-2-ethylpyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 66815206(4-Chloro-2-ethylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (234 mg, 6.2 mmol) was stirred in anhydrous THF (30 mL). A solution of ethyl 4-chloro-2-ethylpyridine-3-carboxylate (878 mg, 4.1 mmol) in anhydrous THF (5 mL) was added at 0° C., and the reaction mixture was stirred at room temperature for 1.5 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-ethylpyridin-3-yl)methanol was obtained as an oil (601 mg, 85% 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-43f87ecf708642ff81925135af2dc378
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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