Water → 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-ethenyl-2-methylbenzoic acid amide

HRID 452525Notes

Reaction equation

HRID 452525 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][CH:17]([C:18]([NH2:20])=[O:19])[C:16]([CH3:24])(C)[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:29](OCC)=[CH2:30].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.O>COCCOC.FC(F)(F)C(O[Pd]OC(=O)C(F)(F)F)=O>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:25]([F:26])([F:27])[F:28])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:20][CH:29]=[CH2:30])=[O:19])=[C:16]([CH3:24])[CH:15]=3)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 13181,10-PhenanthrolineHCID 8023Ethyl vinyl etherHCID 685432824-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-2-meth yl benzoic acid amide

Product 1

HCID 667843634-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-ethenyl-2-methylbenzoic acid amideYield 88%

Reagents, catalysts & solvents 2

HCID 178526102HCID 178526102, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a solution of 0.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-2-methyl benzoic acid amide synthesized in Synthetic Example 29, 0.865 g of ethyl vinyl ether and 0.022 g of 1,10-phenanthroline in 10 ml of 1,2-dimethoxyethane, 0.04 g of bis(trifluoroacetoxy) palladium (II) was added and stirred at room temperature for 19 hours. After the completion of the reaction, 30 ml of water was added in the reaction mixture, and extracted with ethyl acetate (40 ml×1), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, then filtered through silica gel, and the solvent was distilled under reduced pressure to obtain 0.45 g of the aimed product as pale yellow resinous substance.

Workup

  1. additionwas added
  2. additionwas added in the reaction mixture
  3. extractionextracted with ethyl acetate (40 ml×1)
  4. dry with materialdried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order
  5. filtrationfiltered through silica gel
  6. distillationthe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-d17d322d09f64b62ac31d591bbcaff30
Source dataset
uspto-grants-2013_07
Patent number
US08492311B2

Reaction notes

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