Water → HCID 60754547, compound

HRID 230798Notes

Reaction equation

HRID 230798 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:9][C:8]([F:11])([F:10])[C:7]1[C:2]([O:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:18]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 5898332-Chloro-3-(trifluoromethyl)pyridine2×

Product 1

HCID 60754547HCID 60754547, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-3-trifluoromethylpyridine (1.0 g), methyl 4-hydroxybenzenecarboxylate (838.3 mg) and potassium carbonate (2.28 g) were suspended in acetonitrile (10 mL), and heated under reflux for 27 hours, and then 2-chloro-3-trifluoromethylpyridine (1.0 g) was added thereto and further heated under reflux for 24 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 pale yellow oil. The resulting oil was purified through silica gel column chromatography (hexane/ethyl acetate=8/2) to obtain the entitled compound (1.35 g) as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 27 hours
  3. temperaturefurther heated
  4. temperatureunder reflux for 24 hours
  5. extractionextracted with ethyl acetate (100 mL)
  6. 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
  7. dry with materialdried with magnesium sulfate
  8. customevaporated under reduced pressure
  9. customto obtain a pale yellow oil
  10. customThe resulting oil was purified through silica gel column chromatography (hexane/ethyl acetate=8/2)

Sources & evidence

ORD record
ord-7c5220f908e7411896074bf7d4263bd5
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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