Ethanol → Ethyl 4-(hydroxymethyl)picolinate

HRID 1896675Notes

Reaction equation

HRID 1896675 reaction equation
C[Si](Cl)(C)C.[C:6]([C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][N:9]=1)#N.O.C(=O)([O-])[O-:18].[Na+].[Na+].[CH2:23]([OH:25])[CH3:24]>>[CH2:23]([O:25][C:6]([C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][N:9]=1)=[O:18])[CH3:24]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 10340Sodium CarbonateHCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrile

Product 1

HCID 14541449Ethyl 4-(hydroxymethyl)picolinateYield 16%

Procedure

Trimethylsilyl chloride (0.4 mL, 3.0 mmol) was added to a solution of 2-cyanopyridine-4-methanol (200 mg, 1.5 mmol, Reference compound No. 11-1) in ethanol (3 mL) at 50° C. under a nitrogen atmosphere, then the mixture was stirred for 12 hours. The mixture was allowed to stand, and a little water and sodium carbonate (160 mg, 1.5 mmol) were added thereto. The solution was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 43 mg of the title reference compound as a white solid. (Yield 16%)

Workup

  1. dry with materialThe solution was dried over anhydrous magnesium sulfate
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography
  4. customto give 43 mg of the title reference compound as a white solid

Sources & evidence

ORD record
ord-83f5e6d134b84651a5aae4e077f9cfb1
Source dataset
uspto-grants-2013_08
Patent number
US08518973B2

Reaction notes

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