Aluminium lithium hydride → (3-Chloro-5-ethylpyridin-4-yl)methanol

HRID 577102Notes

Reaction equation

HRID 577102 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[C:9]([C:16]([O-])=[O:17])=[C:10]([CH2:14][CH3:15])[CH:11]=[N:12][CH:13]=1>C1COCC1>[Cl:7][C:8]1[CH:13]=[N:12][CH:11]=[C:10]([CH2:14][CH3:15])[C:9]=1[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 866479085-Chloro-3-ethylpyridine-4-carboxylate

Product 1

HCID 59589363(3-Chloro-5-ethylpyridin-4-yl)methanolYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH (0.92 g, 24.24 mmol) in anhydrous THF (20 mL) at 0° C. was added dropwise a solution of 5-chloro-3-ethylpyridine-4-carboxylate (2.59 g, 12.12 mmol) in THF (30 mL). After stirring for 1 hour, the reaction mixture was slowly quenched with 15% NaOH and then diluted with water. Ethyl acetate was added, the mixture was stirred for 10 minutes, and the precipitated white solid was filtered off. The solid was washed with ethyl acetate (2×50 mL). The combined organic layer was separated, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated to provide (3-chloro-5-ethylpyridin-4-yl)methanol as a thick oil (1.83 g, 88% yield), which was used for the next step without any further purification; M+ 166.5.

Workup

  1. customthe reaction mixture was slowly quenched with 15% NaOH
  2. additiondiluted with water
  3. additionEthyl acetate was added
  4. stirringthe mixture was stirred for 10 minutes
  5. filtrationthe precipitated white solid was filtered off
  6. washThe solid was washed with ethyl acetate (2×50 mL)
  7. customThe combined organic layer was separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9633d7dd55ec4d7c83974c9357f2ad14
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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