反应详情

To a stirred mixture of 4-chloro-2-nitrophenol (11.68 g, 67.32 mmol), ethyl 3-phenyloxirane-2-carboxylate (9.61 g, 50.00 mmol) in ethanol (200 mL) was added portionwise 60% sodium hydride (738 mg, 20.00 mmol) and the red mixture stirred at reflux for 3 days. The solvent was removed in vacuo. The residue was dissolved in chloroform and extracted three times with 10% aqueous potassium carbonate. The organic layer was washed with water and brine, dried, filtered and evaporated to afford a brown residue. The residue was dissolved in a minimal volume of chloroform and precipitated by adding diethyl ether to afford the title compound (5.970 g, 33%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ1.16 (t, 3H, J=7.0 Hz), 4.09 (q, 2H, J=7.0 Hz), 4.29 (t, 1H, J=7.0 Hz), 5.63 (d, 1H, J=7.0 Hz), 6.09 (d, 1H, J=7.0 Hz), 7.19-7.60 (m, 7H), 7.97 (d, 1H, J=2.6 Hz). MS APCI, m/z=388 (M+Na). LC/MS: 2.78 min.

1. temperatureat reflux for 3 days
2. customThe solvent was removed in vacuo
3. dissolutionThe residue was dissolved in chloroform
4. extractionextracted three times with 10% aqueous potassium carbonate
5. washThe organic layer was washed with water and brine
6. customdried
7. filtrationfiltered
8. customevaporated
9. customto afford a brown residue
10. customprecipitated
11. additionby adding diethyl ether