Ethyl Acetate → 2-(Hydroxymethyl)-6-methylpyridine-4-carbonitrile

HRID 2071159Notes

Reaction equation

HRID 2071159 reaction equation
FC(F)(F)C([O:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[C:9]([CH3:15])[N:8]=1)=O.C([O-])(O)=O.[Na+].CCOC(C)=O>C1COCC1>[OH:5][CH2:6][C:7]1[CH:12]=[C:11]([CH:10]=[C:9]([CH3:15])[N:8]=1)[C:13]#[N:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 68671186HCID 68671186, compound

Product 1

HCID 178623062-(Hydroxymethyl)-6-methylpyridine-4-carbonitrileYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 1.20 g of (4-cyano-6-methylpyridin-2-yl)methyl 2,2,2-trifluoroacetate in 7 mL of THF was added 7% NaHCO3 (aqueous) solution to pH=8. The mixture was stirred at r.t. for 18 h, and EtOAc was added. The aqueous layer was extracted with EtOAc, and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1 to 6) % MeOH/CHCl3 provided 535 mg of 2-(hydroxymethyl)-6-methylisonicotinonitrile in 73% yield.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography (1 to 6) % MeOH/CHCl3

Sources & evidence

ORD record
ord-64f5df629add4adba89fc830fe77ea3b
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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