反应详情

温度

20 °C

A mixture of 5-(3-hydroxypropyl)-3-methyl-1,2,4-thiadiazole (66 mg, 0.42 mmol), 4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol (94 mg, 0.46 mmol), and DEAD (80 mg, 0.46 mmol) was dissolved in 5 mL of THF. To the above solution was added triphenylphosphine (120 mg, 0.46 mmol) at 0° C. and the mixture was allowed to warm to 20° C. overnight. The solvent was removed in vacuo, an aqueous sodium bicarbonate solution was added, and the mixture was extracted with methylene chloride (3×). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (20 cm column, ethyl acetate/hexane, from 1/6 to 1/4) followed by recrystallization from ethyl acetate/hexane to afford 88 mg (61%) of 3-methyl-5-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6 -dimethylphenoxy]propy]-1,2,4-thiadiazole, as a white crystalline solid, m.p. 67°--71° C.

1. customThe solvent was removed in vacuo
2. additionan aqueous sodium bicarbonate solution was added
3. extractionthe mixture was extracted with methylene chloride (3×)
4. dry with materialThe organic layer was dried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe residue was purified by silica column chromatography (20 cm column, ethyl acetate/hexane, from 1/6 to 1/4)
7. customfollowed by recrystallization from ethyl acetate/hexane