반응 #45888

반응 방정식

hydrochloric acid

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

sodium dihydrogenphosphate dihydrate

2-methyl-2-butene

sodium chlorite

→

4-Cyano-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-6-carboxylic acid

용매

ethyl acetate

tert-butanol

water

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGby stirring at the same temperature for 10 minutes
2. 2
   기타The aqueous layer was separated
3. 3
   추출extracted twice with ethyl acetate
4. 4
   세척washed with saturated brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타The insoluble matter was separated by filtration
7. 7
   기타the solvent was evaporated away
8. 8
   기타to obtain the entitled compound
9. 9
   기타This was used in the next reaction as such

실험 절차

2-Cyclopropyl-7-fluoro-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile (I-182) (160 mg, 0.66 mmol) was dissolved in tert-butanol (4.5 ml)-water (3 ml)-tetrahydrofuran (3 ml), then at 0° C., sodium dihydrogenphosphate dihydrate (153 mg, 0.98 mmol), 2-methyl-2-butene (292 μl, 2.62 mmol), sodium chlorite (purity 80%, 222 mg, 1.97 mmol) were added. This was stirred for 15 hours with gradually warming up to room temperature. At 0° C., aqueous 1 N hydrochloric acid solution and ethyl acetate were added to the reaction liquid, followed by stirring at the same temperature for 10 minutes. The aqueous layer was separated, and 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, the solvent was evaporated away to obtain the entitled compound. This was used in the next reaction as such.

출처