反応 #42580

反応方程式

n-butyllithium

oxazole

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

→

title compound

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

溶媒

ethyl acetate

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度The reaction mixture is heated
2. 2
   温度at reflux for 2 h
3. 3
   温度The reaction mixture is cooled
4. 4
   洗浄washed with water, and saturated sodium chloride
5. 5
   乾燥dried (sodium sulfate)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他Purification by flash column chromatography (silica gel, 60% ethyl acetate/hexane)

実験手順

To a −70° C. stirred solution of oxazole (106 mg, 1.5 mmol) in tetrahydrofuran (4 mL) is added n-butyllithium (1.6 M in hexanes, 1.0 mL, 1.7 mmol). After 30 min, zinc chloride (1 M in diethyl ether, 4.6 mL, 4.6 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-{[ethyl(propyl)amino]carbonyl}-5-iodobenzoate (535 mg, 1.45 mmol) in anhydrous tetrahydrofuran (1.8 mL) followed by palladium(0)tetrakis(triphenylphosphine) (120 mg, 0.10 mmol). The reaction mixture is heated at reflux for 2 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]+.

出典