Water → 2-(4-Fluorobenzoyl)-3-propoxypyridine

HRID 856639Notes

Reaction equation

HRID 856639 reaction equation
C([CH:3]([C:11]1[C:16]([O:17][CH2:18][CH2:19][CH3:20])=[CH:15][CH:14]=[CH:13][N:12]=1)[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)#N.C(=O)([O-])[O-:22].[K+].[K+].O>CS(C)=O.O>[F:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([C:11]2[C:16]([O:17][CH2:18][CH2:19][CH3:20])=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:22])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 229387622-(alpha-Cyano-4-fluorobenzyl)-3-propoxypyridine

Product 1

HCID 229388512-(4-Fluorobenzoyl)-3-propoxypyridineYield 85.8%

Reagents, catalysts & solvents 1

HCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Procedure

Under oxygen atmosphere, a mixed solution of 2-(α-cyano-4-fluorobenzyl)-3-propoxypyridine (5.42 g) and potassium carbonate (3.07 g) in DMSO-water (200-40 ml) was stirred at room temperature for 20 hours. The reaction mixture was added to water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 1:3→1:2), to give 2-(4-fluorobenzoyl)-3-propoxypyridine (4.46 g) as pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained residue was separated
  6. custompurified by column chromatography (ethyl acetate:hexane 1:3→1:2)

Sources & evidence

ORD record
ord-793936c7b05241bdac86b1b253dfbee6
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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