Reaktion #937129

Reaktionsgleichung

3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

compound 1-61

3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

potassium carbonate

methyl bromoacetate

water

→

3-{4-chloro-2-fluoro-5-[(methoxycarbonyl)methoxy]phenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

Ausbeute 53.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   SonstigeAfter completion of the reaction
3. 3
   Extraktionfollowed by extraction with ethyl acetate
4. 4
   WaschenThe organic layer was washed with saturated sodium chloride solution
5. 5
   Trocknendried with anhydrous magnesium sulfate
6. 6
   Einengenconcentrated

Vorschrift

First, 0.15 g of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-61) was dissolved in 0.50 ml of N,N-dimethylformamide, to which 97 mg of potassium carbonate and 48 μl of methyl bromoacetate were added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 97 mg (yield, 53%) of 3-{4-chloro-2-fluoro-5-[(methoxycarbonyl)methoxy]phenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-165; m.p., 116.6° C.).

Quelle