반응 #68019
ord-9af1d405f51242f9898f02c277824429
반응 방정식
반응 조건
후처리
- 1workup.ADDITIONwere added
- 2온도with reflux
- 3온도by heating under a nitrogen atmosphere
- 4workup.STIRRINGthe mixture was stirred at 90 to 100° C. for 1 hour
- 5workup.STIRRINGthe mixture was stirred at 90 to 100° C. for 1 hour
- 6기타the organic layer was separated
- 7추출the aqueous layer was extracted with ethyl acetate
- 8세척the resultant solution was washed sequentially with water
- 9건조an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
- 10기타the solvent was removed under reduced pressure
- 11기타The residue thus obtained
- 12기타was purified by flash silica gel column chromatography [hexane:gradient elution of ethyl acetate=95:5 to 80:20]
실험 절차
To 30 mL of a 1,4-dioxane solution containing 2.4 g of 2-chloro-5-fluoro-3-((methoxymethoxy)methyl)-6-methylpyridine, 2.3 mL of triethylamine, 0.61 mL of formic acid and 0.63 g of tetrakis(triphenylphosphine)palladium(0) were added, and the mixture was stirred for 2 hours with reflux by heating under a nitrogen atmosphere. Thereto was added 30 mL of N,N-dimethylformamide, and the mixture was stirred at 90 to 100° C. for 1 hour. Thereto were added 2.3 mL of triethylamine, 0.61 mL of formic acid and 0.63 g of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 90 to 100° C. for 1 hour. Water and ethyl acetate were added thereto, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, and the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by flash silica gel column chromatography [hexane:gradient elution of ethyl acetate=95:5 to 80:20] to obtain 1.8 g of a yellow oily substance, 3-fluoro-5-((methoxymethoxy)methyl)-2-methylpyridine.