Réaction #2254181

Équation de réaction

5-(hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene

Chlorox

NaOH

→

5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

Rendement 15.7%

Solvants

THF

diethyl ether

Conditions de réaction

Traitement

1. 1
   AutreThe cold bath is then removed
2. 2
   workup.ADDITIONwater is added
3. 3
   Extractionthe reaction mixture is extracted three times with ethyl acetate
4. 4
   Séchagedried over Na2SO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe crude product is purified on a semi-preparative HPLC

Mode opératoire

Chlorox (4%, 1.02 nil) and NaOH (1N, 0.1 ml) are premixed and then added to a solution of 5-(hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (200 mg) and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (170 mg, example 1, Step A) in THF (3 ml) and diethyl ether (3 ml) at 5° C. The cold bath is then removed. After 21 hours, water is added and the reaction mixture is extracted three times with ethyl acetate. The organic phases are combined, dried over Na2SO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (56 mg) as light yellow oil. MS (HPLC/MS): 505 (MH+). Retention time: 4.38 min.

Source