反应详情

2.00 g of ethyl 5-(1-hydroxy-1-methylethyl)isoxazole-3-carboxylate was dissolved in 20 ml of tetrahydrofuran, and 0.44 g of sodium hydride and 1.32 g of 3-bromo-1-propyne were then added under ice-cooling. The mixture was stirred at room temperature for 5 hours. After water was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and then recrystallized from hexane-ethyl acetate to obtain 0.25 g of ethyl 5-[1-methyl-1-(2-propynyloxy)ethyl]isoxazole-3-carboxylate.

1. temperaturecooling
2. extractionthe reaction mixture was extracted with methyl-t-butyl ether
3. washThe organic layer was washed with water
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customrecrystallized from hexane-ethyl acetate