反应详情

温度

95 °C

A mixture of 3-pyridin-3-yl-phenol (5.14 g, 30.0 mmol), ethyl 2-bromoisobutyrate (26.3 g, 135.0 mmol), and K2CO3 (18.7 g, 135.0 mmol) in anhydrous DMF (60 mL) was heated at 95° C. under nitrogen for 5 h. After cooling, brine (200 mL) was added and the mixture was extracted with ethyl acetate (250 mL). The separated organic layer was washed with brine, filtered, and concentrated. The oil residue was taken up in 80 mL of 3 M HCl, stirred for 15 min, diluted with brine (100 mL), and extracted with ethyl acetate (2×150 mL). The separated aqueous layer was cooled in ice/water bath, adjusted to pH 10 with solid Na2CO3, and extracted with ethyl acetate (2×200 mL). The organic extract was dried over sodium sulfate and concentrated to afford 6.70 g (78%) of 2-methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl ester as a light brown oil: 1H NMR (CDCl3) δ 1.22 (t, 3H), 1.61 (s, 6H), 4.22 (q, 2H), 6.82 (dd, 1H), 7.08 (s, 1H), 7.20 (dd, 1H), 7.38 (m, 2H), 7.81 (dd, 1H), 8.59 (br s, 1H), 8.80 (br s, 1H); MS m/z (relative intensity) 285 (M+, 11), 212 (22), 171 (100).

1. temperatureAfter cooling
2. extractionthe mixture was extracted with ethyl acetate (250 mL)
3. washThe separated organic layer was washed with brine
4. filtrationfiltered
5. concentrationconcentrated
6. additiondiluted with brine (100 mL)
7. extractionextracted with ethyl acetate (2×150 mL)
8. temperatureThe separated aqueous layer was cooled in ice/water bath
9. extractionextracted with ethyl acetate (2×200 mL)
10. extractionThe organic extract
11. dry with materialwas dried over sodium sulfate
12. concentrationconcentrated