反应详情

温度

0 °C

A mixture of 6-(3,3,3-trifluoropropoxy)-2,3-dihydro-1H-inden-1-one (Intermediate 16, 0.774 g, 3.17 mmol) and methyl acrylate (0.629 mL, 6.97 mmol) in 2-Me THF (4 mL) was cooled to 0° C. and potassium tert-butoxide (0.427 g, 3.80 mmol) was added in portions. After stirring for 1.5 h at r.t., water (6.0 mL) and potassium hydroxide (0.178 g, 3.17 mmol) were added and the mixture was heated at reflux overnight. The mixture was cooled to r.t. and water and brine was added. The layers were separated and the aqueous layer extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated yielding the title compound (689 mg, 67% yield). 1H NMR (500 MHz, CDCl3) δ ppm 1.82-1.92 (m, 2 H), 2.17-2.27 (m, 2 H), 2.42-2.53 (m, 2 H), 2.60-2.75 (m, 4 H), 3.14-3.20 (m, 2 H), 4.22-4.27 (m, 2 H), 7.19-7.22 (m, 1 H), 7.25 (dd, 1 H), 7.41 (d, 1 H): MS (ES+) m/z 327 [M+H]+.

1. temperaturethe mixture was heated
2. temperatureat reflux overnight
3. temperatureThe mixture was cooled to r.t.
4. customThe layers were separated
5. extractionthe aqueous layer extracted with EtOAc
6. dry with materialThe combined organic layers were dried over MgSO4
7. concentrationconcentrated