Reacción #45864

Ecuación de reacción

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

Super Hydride

ammonium chloride

→

compound

Rendimiento 95.0%

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

Rendimiento 95.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente