Potassium Carbonate → (6-Fluoropyridin-2-yl)methanol

HRID 2182137Notes

Reaction equation

HRID 2182137 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[N:4]=1.C([O-])([O-])=[O:11].[K+].[K+]>O>[F:9][C:5]1[N:4]=[C:3]([CH2:2][OH:11])[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 224820332-(Chloromethyl)-6-fluoropyridine

Product 1

HCID 12045263(6-Fluoropyridin-2-yl)methanolYield 41.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-chloromethyl-6-fluoro-pyridine I-3c (1.43 g, 9.84 mmol) in H2O (22 mL) was added K2CO3 (1.77 g, 12.8 mmol). The reaction mixture was stirred overnight at reflux. The cooled aqueous mixture was first extracted with heptane (2×20 mL)and then ethyl acetate (2×50 mL). The ethyl acetate layers were combined, washed with brine, dried (Na2SO4), and concentrated to dryness. The crude residue was chromatographed over silica gel (15 g) using 2% methanol/methylene chloride with 0.5% NH4OH as the eluant to yield 518.7 mg of the title compound (I-3d) as a yellow oil.

Workup

  1. temperatureat reflux
  2. extractionThe cooled aqueous mixture was first extracted with heptane (2×20 mL)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to dryness
  6. customThe crude residue was chromatographed over silica gel (15 g)

Sources & evidence

ORD record
ord-5129a563af974c55b11aba1ec0605773
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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