Ethyl Acetate → (6-Methoxypyridin-3-yl)methanol

HRID 1948223Notes

Reaction equation

HRID 1948223 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][N:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O>C1COCC1.O>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([CH2:7][OH:8])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 33645766-Methoxypyridine-3-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 12259941(6-Methoxypyridin-3-yl)methanolYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 16 Method A: A solution of 6-methoxynicotinaldehyde (1 eq, 2.19 mmol, 0.30 g) and LiAlH4 (0.5 eq, 1.05 mmol, 0.04 g) in THF (10 mL) was stirred for 30 min. at 0° C. and overnight at room temperature. After the addition of AcOEt, the reaction mixture was diluted with water. The organic layer washed with saturated NH4Cl solution, dried over Na2SO4, filtered and evaporated. The resulting crude residue was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 80/20 to afford (6-methoxypyridin-3-yl)methanol (1.80 mmol, 0.26 g, 90%) as a pale oil.

Workup

  1. washThe organic layer washed with saturated NH4Cl solution
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting crude residue was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2)

Sources & evidence

ORD record
ord-88dd12fd0d914213a57bd8b36bd5a311
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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