تفاعل #2254181

معادلة التفاعل

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

المردود 15.7%

المذيبات

THF

diethyl ether

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر