Water → HCID 22259358, compound

HRID 1610974Notes

Reaction equation

HRID 1610974 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:36]=[CH:35][C:15]([O:16][CH2:17][C:18]2[N:19]=[C:20](/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[O:21][CH:22]=2)=[CH:14][CH:13]=1.[NH:37]1[CH:41]=[C:40]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[N:39]=[N:38]1.O>CN(C)C=O>[F:32][C:31]([F:34])([F:33])[C:28]1[CH:29]=[CH:30][C:25](/[CH:24]=[CH:23]/[C:20]2[O:21][CH:22]=[C:18]([CH2:17][O:16][C:15]3[CH:35]=[CH:36][C:12]([CH2:11][CH2:10][CH2:9][CH2:8][N:37]4[CH:41]=[C:40]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[N:39]=[N:38]4)=[CH:13][CH:14]=3)[N:19]=2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22259303HCID 22259303, compoundHCID 178469944HCID 178469944, compound

Product 1

HCID 22259358HCID 22259358, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Potassium carbonate (2.4 g) was added to a solution of 4-[[4-(4-iodobutyl)phenoxy]methyl]-2-{(E)-2-[4-(trifluoromethyl)phenyl]ethenyl}-1,3-oxazole (7.5 g) and ethyl 1H-1,2,3-triazole-4-carboxylate (2.1 g) in dimethylformamide (100 ml), and the mixture was stirred at 70° C. for 5 hr. After the reaction was completed, the reaction mixture was combined with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=3:1), and recrystallized from ethyl acetate-hexane to give the titled compound (1.85 g) as a colorless crystal powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=3:1)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-20277d56cb6945349e7c7029359bf3f3
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

Loading…