反応 #2254181

反応方程式

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

収率 15.7%

溶媒

THF

diethyl ether

反応条件

後処理

1. 1
   その他The cold bath is then removed
2. 2
   workup.ADDITIONwater is added
3. 3
   抽出the reaction mixture is extracted three times with ethyl acetate
4. 4
   乾燥dried over Na2SO4
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The crude product is purified on a semi-preparative HPLC

実験手順

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.

出典