Triethylamine → HCID 58047403, compound

HRID 1888710Notes

Reaction equation

HRID 1888710 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:22]([O:24][C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([O:9][CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=2)=[CH:27][CH:26]=1)[CH3:23]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 121504-EthoxyphenolHCID 31297Methanesulfonyl chlorideHCID 11332468(2-Fluoropyridin-4-yl)methanol

Product 1

HCID 58047403HCID 58047403, compoundYield 8.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-fluoropyridin-4-yl)methanol (5.06 g, 39.8 mmol) in DMF (100 mL) were added triethylamine (8.30 mL, 59.7 mmol) and methanesulfonyl chloride (3.08 mL, 39.8 mmol) under ice-cooling. After stirring for 30 min, 4-ethoxyphenol (5.77 g, 41.8 mmol) and potassium carbonate (5.50 g, 39.8 mmol) were added thereto and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added ethyl acetate, and the mixture was washed with water, 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3). A mixture of the obtained product and 4-ethoxyphenol (starting material) was purified again by basic silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to give the title compound (822 mg, yield 8.4%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 16 hr
  3. washthe mixture was washed with water, 10% aqueous potassium carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3)
  7. additionA mixture of the obtained product and 4-ethoxyphenol (starting material)
  8. customwas purified again by basic silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3)

Sources & evidence

ORD record
ord-bb7ffe6e42294414bd7481014390e818
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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