Benzaldehyde → 3-(3,4-Difluoro-phenyl)-5-([E]-styryl)-isoxazole-4-carboxylic acid

HRID 1514704Notes

Reaction equation

HRID 1514704 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[O-]CC.[Na+].Cl>C(O)C>[F:19][C:14]1[CH:13]=[C:12]([C:7]2[C:6]([C:4]([OH:3])=[O:5])=[C:10](/[CH:11]=[CH:20]/[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:9][N:8]=2)[CH:17]=[CH:16][C:15]=1[F:18]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 57466747Ethyl 3-(3,4-difluorophenyl)-5-methylisoxazole-4-carboxylate

Product 1

HCID 667181913-(3,4-Difluoro-phenyl)-5-([E]-styryl)-isoxazole-4-carboxylic acidYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3-(3,4-difluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (50 g, 187 mmol) and benzaldehyde (19.1 mL, 187 mmol) in ethanol (280 mL) was added sodium ethoxide (2.71 M, 75.8 mL, 206 mmol) and the reaction was stirred at reflux for 1 h. Hydrochloric acid (1 N, 225 mL) was added and the resulting mixture was then triturated with dichloromethane and filtered to afford the title compound (53.5 g, 87%) as a light yellow solid. MS: m/e=328.3 [M+H]+.

Workup

  1. temperatureat reflux for 1 h
  2. customthe resulting mixture was then triturated with dichloromethane
  3. filtrationfiltered

Sources & evidence

ORD record
ord-e5ff938855c14e49b1d35c8c6c9a3108
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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