HCID 5323747, compound → HCID 45080047, compound

HRID 630230Notes

Reaction equation

HRID 630230 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]1[CH:10]=[C:11]([C:15](OC)=[O:16])[CH:12]=[N:13][CH:14]=1)[CH3:8]>C1COCC1>[CH2:7]([C:9]1[CH:10]=[C:11]([CH2:15][OH:16])[CH:12]=[N:13][CH:14]=1)[CH3:8]

Participants

4

Reactant 2

HCID 5323747HCID 5323747, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 45080047HCID 45080047, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH (1.92 g, 50.85 mmol) in anhydrous THF 40 mL at 0° C. was added dropwise a solution of methyl 5-ethylpyridine-3-carboxylate (4.20 g, 25.42 mmol) in THF (50 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 reaction mixture was stirred for 10 minutes, and the precipitate was filtered off. The solid was washed with ethyl acetate (3×100 mL). The filtrate was dried over anhydrous sodium sulfate, filtered, and evaporated to provide (5-ethylpyridin-3-yl)methanol as a thick oil (3.31 g, 95% yield), which was used in the next step without any further purification; M+137.18.

Workup

  1. customthe reaction mixture was slowly quenched with 15% NaOH
  2. additiondiluted with water
  3. additionEthyl acetate was added
  4. stirringthe reaction mixture was stirred for 10 minutes
  5. filtrationthe precipitate was filtered off
  6. washThe solid was washed with ethyl acetate (3×100 mL)
  7. dry with materialThe filtrate was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-bdbcf056342543c4bb3f8487061c7f6d
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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