반응 #42344
ord-d945e176239c4c6c9e6013b66b49819e
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후처리
- 1온도The reaction mixture is heated
- 2온도at reflux for 2 h
- 3온도The reaction mixture is cooled
- 4세척washed with water, and brine
- 5건조dried (sodium sulfate)
- 6여과filtered
- 7농축concentrated under reduced pressure
- 8기타Purification by flash column chromatography (silica gel, 60% ethyl acetate/hexane)
- 9기타provides a solid
- 10workup.ADDITIONis added
- 11세척washed with 1N hydrochloric acid (aq), water, and brine
- 12건조dried (sodium sulfate)
- 13여과filtered
- 14농축concentrated under reduced pressure
실험 절차
To a −70° C. stirred solution of oxazole (330 mg, 4.8 mmol) in tetrahydrofuran (4 mL) is added n-butyllithium (1.6 M in hexanes, 3.3 mL, 5.3 mmol). After 30 min, zinc chloride (1 M in diethyl ether, 14.5 mL, 14.5 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-iodo-5-{[methyl(propyl)amino]carbonyl}benzoate (1.6 g, 4.5 mmol) in anhydrous tetrahydrofuran (3 mL) followed by palladium(0)tetrakis(triphenylphosphine) (221 mg, 0.19 mmol). The reaction mixture is heated at reflux for 2 h. The reaction mixture is cooled, diluted with ethyl acetate, washed with water, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 60% ethyl acetate/hexane) provides a solid. The solid is redissolved in 1:1:1 tetrahydrofuran/methanol/water (9 mL), and lithium hydroxide monohydrate (311 mg, 7.4 mmol) is added and stirred 2 h at room temperature. The reaction is diluted in chloroform and washed with 1N hydrochloric acid (aq), water, and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to give the title compound. ESI MS m/z 287.3 [M−H]−.