反应详情

Sodium metal (1.68 g, 73 mg atom) was dissolved in ethanol (160 mL) and 3-hydroxycinnamic acid (10 g, 6 mmol) added. After stirring for 5 minutes, concentrated H2SO4 (4 drops) was added followed by 2-bromo-2-phenoxyacetophenone (16.76 g, 6 mmol) and the mixture heated to reflux. After 135 minutes, the mixture was cooled, diluted with water and extracted with CH2Cl2. The combined extracts were dried over sodium sulfate and concentrated to leave an oil which was dissolved in acetic acid (110 mL). Ammonium acetate (23.47 g, 300 mmol) was added and the mixture heated to reflux. After 75 minutes, the solution was cooled, diluted with water and extracted with CH2Cl2. The organic extracts were dried over sodium sulfate and the solvent evaporated to leave a khaki solid that was triturated with diethyl ether to give (10.80 g, 52%). Recrystallization of a 1.5 g sample from ethanol gave 0.7 g of analytically pure 3-[2-(4,5-diphenyl2-oxazolyl)ethenyl]phenol, m.p. 201°-203° C.

1. temperaturethe mixture heated to reflux
2. waitAfter 135 minutes
3. temperaturethe mixture was cooled
4. extractionextracted with CH2Cl2
5. dry with materialThe combined extracts were dried over sodium sulfate
6. concentrationconcentrated
7. customto leave an oil which
8. temperaturethe mixture heated to reflux
9. waitAfter 75 minutes
10. temperaturethe solution was cooled
11. extractionextracted with CH2Cl2
12. dry with materialThe organic extracts were dried over sodium sulfate
13. customthe solvent evaporated
14. customto leave a khaki solid
15. customthat was triturated with diethyl ether
16. customto give (10.80 g, 52%)
17. customRecrystallization of a 1.5 g sample from ethanol