反应详情

Sodium metal (1.00 g, 43 mg atom) was dissolved in ethanol (125 mL) and 3-(4-hydroxyphenyl)propionic acid (6.04 g, 36 mmol) added to give a white precipitate. The mixture was warmed briefly with stirring and concentrated H2SO4 (3 drops) added followed by 2-bromo-2-phenylacetophenone (1.00 g, 36 mmol). The mixture was heated at reflux for 2 hours, cooled, concentrated and diluted with water. The mixture was extracted with CH2Cl2, the combined extracts dried over sodium sulfate and concentrated to give an oil which was dissolved in acetic acid (250 mL). Ammonium acetate (14.00 g, 180 mmol) was added and the mixture heated to reflux. After 100 minutes, the solution was cooled, diluted with water and extracted with CH2Cl2. The combined extracts were dried over sodium sulfate and the solvent evaporated to leave a solid that was triturated with a mixture of hexanes and diethyl ether and filtered to give 4-[2 -(4,5-diphenyl-2-oxazolyl)ethyl]phenol (8.00 g, 64%). An analytical sample was prepared by recrystallizing 1.5 g from a mixture of hexanes and CH2Cl2 to give 1.20 g of pure material, m.p. 142°-144° C.

1. customto give a white precipitate
2. temperatureThe mixture was warmed briefly
3. temperatureThe mixture was heated
4. temperatureat reflux for 2 hours
5. temperaturecooled
6. concentrationconcentrated
7. additiondiluted with water
8. extractionThe mixture was extracted with CH2Cl2
9. dry with materialthe combined extracts dried over sodium sulfate
10. concentrationconcentrated
11. customto give an oil which
12. temperaturethe mixture heated to reflux
13. temperaturethe solution was cooled
14. extractionextracted with CH2Cl2
15. dry with materialThe combined extracts were dried over sodium sulfate
16. customthe solvent evaporated
17. customto leave a solid
18. customthat was triturated with a mixture of hexanes and diethyl ether
19. filtrationfiltered