反应详情

温度

78 °C

To a stirring solution of 2-(3-fluorophenyl)oxirane (5.60 g, 40.5 mmol) in toluene (65 ml) was added 4-hydroxybenzaldehyde (7.40 g, 61.0 mmol), 1M NaOH (65 ml) and PEG4000 (polyethylene glycol, 0.85 g) and the stirring mixture was heated at 78° C. overnight. The reaction mixture was allowed to cool to RT and then extracted with EtOAc (2×150 ml). The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting light brown oil was chromatographed eluting with 30-40% EtOAc/hexanes. There are 2 major spots. Fractions containing the higher Rf spot were combined and evaporated in vacuo to give 1.78 g (17%) of the title compound as a white solid. Fractions containing the lower Rf spot were combined and evaporated in vacuo to give 0.90 g (9%) of the regioisomer as a nearly colorless oil.

1. temperatureto cool to RT
2. extractionextracted with EtOAc (2×150 ml)
3. washThe combined extracts were washed with brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. customevaporated in vacuo
7. customThe resulting light brown oil was chromatographed
8. washeluting with 30-40% EtOAc/hexanes
9. additionFractions containing the higher Rf spot
10. customevaporated in vacuo