Water → HCID 68998985, compound

HRID 230796Notes

Reaction equation

HRID 230796 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:8][C:4]1[N:3]=[C:2]([O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 739342,6-Difluoropyridine

Product 1

HCID 68998985HCID 68998985, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,6-Difluoropyridine (1.0 g), methyl 4-hydroxybenzenecarboxylate (1.32 g) and potassium carbonate (3.60 g) were suspended in acetonitrile (10 mL), and heated under reflux for 21 hours. Water (100 mL) was added to the reaction liquid, extracted with ethyl acetate (100 mL), and the organic layer was washed with aqueous 2 N sodium hydroxide solution (100 mL), water (100 mL) and saturated saline water (100 mL) in that order, dried with magnesium sulfate, and evaporated under reduced pressure to obtain a colorless oil. The resulting oil was purified through silica gel column chromatography (hexane/ethyl acetate=10/0 to 7/3) to obtain the entitled compound (1.48 g) as a colorless solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 21 hours
  3. extractionextracted with ethyl acetate (100 mL)
  4. washthe organic layer was washed with aqueous 2 N sodium hydroxide solution (100 mL), water (100 mL) and saturated saline water (100 mL) in that order
  5. dry with materialdried with magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto obtain a colorless oil
  8. customThe resulting oil was purified through silica gel column chromatography (hexane/ethyl acetate=10/0 to 7/3)

Sources & evidence

ORD record
ord-beaf8199f9bc4bb0903de0d1af2598bc
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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