反应详情

温度

93 °C

A mixture of 3-pyridin-3-yl-phenol (0.86 g, 5.0 mmol), methyl 2-bromoisobutyrate (3.60 g, 20.0 mmol), and K2CO3 (2.76 g, 20.0 mmol) in anhydrous DMF (10 mL) was heated at 93° C. under nitrogen for 3 h. After cooling, brine (40 mL) was added and the mixture was extracted with ethyl acetate (50 mL). The separated organic layer was washed with brine, filtered, and concentrated. The oil residue was taken up in 10 mL of 3 M HCl, stirred for 10 min, diluted with brine (10 mL), and extracted with ethyl acetate (2×30 mL). The separated aqueous layer was cooled in ice/water bath, adjusted to pH 10 with solid Na2CO3, and extracted with ethyl acetate (2×40 mL). The organic extract was dried over sodium sulfate and concentrated to afford 1.09 g (80%) of 2-methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid methyl ester as a yellow oil: 1H NMR (CDCl3) δ 1.62 (s, 6H), 3.79 (s, 3H), 6.82 (dd, 1H), 7.08 (s, 1H), 7.20 (d, 1H), 7.38 (m, 2H), 7.81 (d, 1H), 8.59 (d, 1H), 8.80 (s, 1H); MS m/z (relative intensity) 271 (M+, 20), 212 (30), 171 (100).

1. temperatureAfter cooling
2. extractionthe mixture was extracted with ethyl acetate (50 mL)
3. washThe separated organic layer was washed with brine
4. filtrationfiltered
5. concentrationconcentrated
6. additiondiluted with brine (10 mL)
7. extractionextracted with ethyl acetate (2×30 mL)
8. temperatureThe separated aqueous layer was cooled in ice/water bath
9. extractionextracted with ethyl acetate (2×40 mL)
10. extractionThe organic extract
11. dry with materialwas dried over sodium sulfate
12. concentrationconcentrated