反应详情

Sodium hydride (0.9 g; 60% in oil) was added to 20 ml of toluene, and with heating, a solution of 2.5 g of 2-(4-methylphenyl)-2-methylpropyl alcohol in 10 ml of a mixture of 25% dimethylformamide and toluene was added dropwise over the course of 15 minutes. The mixture was stirred for 10 minutes, and then a solution of 2.9 g of 4-(2-fluoroethoxy)benzyl chloride in 10 ml of toluene was added dropwise over the course of 20 minutes. The mixture was further heated under reflux for 1 hour. The reaction mixture was cooled to room temperature, poured into water, and then extracted with toluene. The toluene layer was washed with water and dried over anhydrous sodium sulfate. Toluene was evaporated under reduced pressure. The resulting crude ether was purified by silica gel (100 g) column chromatography (developing solvent: a 2:1 mixture of toluene and n-hexane) to give 3.3 g of the desired 4-(2-fluoroethoxy)benzyl 2-(4-methylphenyl)-2-methylpropyl ether.

1. temperaturewith heating
2. temperatureThe mixture was further heated
3. temperatureunder reflux for 1 hour
4. extractionextracted with toluene
5. washThe toluene layer was washed with water
6. dry with materialdried over anhydrous sodium sulfate
7. customToluene was evaporated under reduced pressure
8. customThe resulting crude ether was purified by silica gel (100 g) column chromatography (
9. additiona 2:1 mixture of toluene and n-hexane)