반응 #45866

반응 방정식

vinylmagnesium bromide

2-cyclopropyl-7-(l iodomethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

ammonium chloride

→

compound

수율 73.0%

7-(1-Allylbut-3-enyl)-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

수율 73.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONwas gradually added
2. 2
   workup.STIRRINGAfter stirring at the same temperature for 1 hour and 20 minutes
3. 3
   workup.STIRRINGby further stirring for 30 minutes
4. 4
   추출This was extracted three times with ethyl acetate
5. 5
   세척washed with saturated brine
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   기타The insoluble matter was separated by filtration
8. 8
   기타the solvent was evaporated away
9. 9
   기타the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

실험 절차

Copper (I) iodide (52 mg, 0.27 mmol) was suspended in tetrahydrofuran (3 ml), and under nitrogen atmosphere at −30° C., vinylmagnesium bromide (1 M tetrahydrofuran solution) (2.72 ml, 2.72 mmol) was dropwise added. The solution was stirred at the same temperature for 30 minutes, then a solution of 2-cyclopropyl-7-(l iodomethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-298)(425 mg, 0.91 mmol) dissolved in tetrahydrofuran (6 ml) was gradually added. After stirring at the same temperature for 1 hour and 20 minutes and heating up to 0° C., aqueous saturated ammonium chloride solution was added, followed by further stirring for 30 minutes. This was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=9:1, v/v) to obtain the entitled compound (243 mg, 73%) as a colorless gel.

출처