반응 #45864

반응 방정식

Methyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)pent-4-enate

Super Hydride

ammonium chloride

→

compound

수율 95.0%

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

수율 95.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGby further stirring at room, temperature for 10 minutes
2. 2
   추출The solution was extracted three times with ethyl acetate
3. 3
   세척washed with saturated brine
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   기타The insoluble matter was separated by filtration
6. 6
   기타the solvent was evaporated away
7. 7
   기타the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

실험 절차

Methyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)pent-4-enate (I-296) (100 mg, 0.26 mmol) was dissolved in tetrahydrofuran (2 ml), then under nitrogen atmosphere at −78° C., Super Hydride (1.0 M tetrahydrofuran solution) (570 μl, 0.52 mmol) was dropwise added. After stirring at the same temperature for 2 hours, aqueous saturated ammonium chloride solution was added, followed by further stirring at room, temperature for 10 minutes. The solution was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, 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=2:1, v/v) to obtain the entitled compound (88 mg, 95%) as a colorless gel.

출처