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

HRID 630140Notes

Reaction equation

HRID 630140 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:9]([C:16](OCC)=[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 59589416Ethyl 5-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 lithium aluminum hydride (LAH, 0.920 g, 24.24 mmol) in anhydrous THF (20 mL) at 0° C. was added dropwise a solution of ethyl 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% aqueous NaOH and then water. Ethyl acetate was added, and the mixture was stirred for 10 minutes. The white precipitate was filtered off and washed with ethyl acetate (2×50 mL). The combined organic layer was 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) and used for the next step without any further purification; M+166.5.

Workup

  1. customthe reaction mixture was slowly quenched with 15% aqueous NaOH
  2. additionEthyl acetate was added
  3. stirringthe mixture was stirred for 10 minutes
  4. filtrationThe white precipitate was filtered off
  5. washwashed with ethyl acetate (2×50 mL)
  6. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-eabb784b974c4d758abf696bd4953422
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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