반응 #45742

반응 방정식

trimethylsilyldiazomethane diethyl ether

sodium dihydrogenphosphate dihydrate

2-methyl-2-butene

sodium chlorite

sodium hydrogencarbonate

hydrochloric acid

2-Cyclopropyl-7-fluoro-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile

→

Methyl 4-cyano-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-6-carboxylate

용매

water

tetrahydrofuran

ethyl acetate

tert-butanol

반응 조건

후처리

1. 1
   기타the solvent was evaporated away under reduced pressure
2. 2
   추출The aqueous layer was further extracted twice 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 under reduced pressure
7. 7
   workup.ADDITIONBenzene (6 ml) and methanol (2 ml) were added to it
8. 8
   workup.STIRRINGAfter stirring at room temperature for 18 hours
9. 9
   추출The solution was extracted three times with ethyl acetate
10. 10
    세척washed with saturated brine
11. 11
    건조dried over anhydrous sodium sulfate

실험 절차

2-Cyclopropyl-7-fluoro-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile (I-182) (280 mg, 1.15 mmol) was dissolved in tert-butanol (8 ml), tetrahydrofuran (6 ml) and water (6 ml), then at 0° C., sodium dihydrogenphosphate dihydrate (268 mg, 1.72 mmol), 2-methyl-2-butene (515 μl, 4.59 mmol), then sodium chlorite (purity 80%, 389 mg, 3.44 mmol) were added. After stirring at room temperature for 6 hours, the solvent was evaporated away under reduced pressure. The residue was fractionated with ethyl acetate and aqueous 1 mol hydrochloric acid solution. The aqueous layer was further extracted twice 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, then the solvent was evaporated away under reduced pressure. Benzene (6 ml) and methanol (2 ml) were added to it, then at 0° C., 2 M trimethylsilyldiazomethane/diethyl ether solution (1.15 ml, 2.29 mmol) was added. After stirring at room temperature for 18 hours, an aqueous saturated sodium hydrogencarbonate solution was added at 0° C. The solution was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate.

출처