Reaktion #2254181

Reaktionsgleichung

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

Ausbeute 15.7%

Lösungsmittel

THF

diethyl ether

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle