Methyl Acrylate → 6'-(3,3,3-Trifluoropropoxy)spiro[cyclohexane-1,2'-indene]-1',4(3'H)-dione

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence