反应详情

温度

78 °C

To a stirring solution of 2-(2-fluorophenyl)oxirane (5.30 g, 38.4 mmol) in toluene (65 mL) was added 4-hydroxybenzaldehyde (7.0 g, 58.0 mmol), 1M NaOH (65 mL) and PEG4000 (polyethylene glycol, 0.85 g) and the stirring mixture was heated at 78° C. overnight. The reaction 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 adsorbed onto silica gel and chromatographed, eluting with 30-40% EtOAc/hexanes to give 2 major spots. Fractions containing the higher Rf spot were combined and evaporated in vacuo to give 1.10 g (11%) of the title compound as a colorless oil. Fractions containing the lower Rf spot were combined and evaporated in vacuo to give 0.67 g (7%) of the regioisomer as a 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. customchromatographed
8. washeluting with 30-40% EtOAc/hexanes
9. customto give 2 major spots
10. additionFractions containing the higher Rf spot
11. customevaporated in vacuo