反応 #45864

反応方程式

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

Super Hydride

ammonium chloride

→

compound

収率 95.0%

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

収率 95.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGby further stirring at room, temperature for 10 minutes
2. 2
   抽出The solution was extracted three times with ethyl acetate
3. 3
   洗浄washed with saturated brine
4. 4
   乾燥dried over anhydrous sodium sulfate
5. 5
   その他The insoluble matter was separated by filtration
6. 6
   その他the solvent was evaporated away
7. 7
   その他the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

実験手順

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.

出典