Реакция #2254181

Уравнение реакции

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

Выход 15.7%

Растворители

THF

diethyl ether

Условия реакции

Обработка

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

Методика

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.

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