반응 #42576

반응 방정식

n-butyllithium

oxazole

methyl 3-{[butyl(methyl)amino]carbonyl}-5-iodobenzoate

→

title compound

Methyl 3-{[butyl(methyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoate

용매

ethyl acetate

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The reaction mixture is heated
2. 2
   온도at reflux for 1.5 h
3. 3
   온도The reaction mixture is cooled
4. 4
   세척washed with water, and saturated sodium chloride
5. 5
   건조dried (sodium sulfate)
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타Purification by flash column chromatography (silica gel, 60% ethyl acetate/hexane)

실험 절차

To a −70° C. stirred solution of oxazole (167 mg, 2.4 mmol) in tetrahydrofuran (4 mL) is added n-butyllithium (1.6 M in hexanes, 1.7 mL, 2.7 mmol). After 30 min, zinc chloride (1 M in diethyl ether, 7.3 mL, 7.3 mmol) is added and the reaction mixture is warmed to 0° C. for 1 h. To this mixture is added a solution of methyl 3-{[butyl(methyl)amino]carbonyl}-5-iodobenzoate (864 mg, 2.3 mmol) in anhydrous tetrahydrofuran (3 mL) followed by palladium(0)tetrakis(triphenylphosphine) (112 mg, 0.10 mmol). The reaction mixture is heated at reflux for 1.5 h. The reaction mixture is cooled, diluted with ethyl acetate, washed with water, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 60% ethyl acetate/hexane) provides the title compound. ESI MS m/z 317.1 [M+H]+.

출처