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

Participants

Reaction Steps

Potassium tert-butoxide (7.50 g, 66.81 mmol) was added in portions to 6-bromo-2,3-dihydro-1H-inden-1-one (11.75 g, 55.67 mmol) and methyl acrylate (11.05 mL, 122.5 mmol) in THF (55 mL) under cooling in an ice-bath. The mixture was stirred for 1.5 h at r.t. Water (80 mL) and KOH (3.12 g, 55.7 mmol) was added and the mixture was heated to 75° C. and then at 60° C. overnight. The mixture was cooled to 0° C., and the formed precipitate was filtered off and dried in vacuo to give the title compound (11.69 g, 72% yield). 1H NMR (500 MHz, CDCl3) δ ppm 1.83-1.92 (m, 2 H), 2.15-2.27 (m, 2 H), 2.40-2.50 (m, 2 H), 2.71 (dt, 2 H), 3.17 (s, 2 H), 7.39 (d, 1 H), 7.75 (dd, 1 H), 7.92 (d, 1 H); MS (ES+) m/z 293 [M+H]+.

Provenance & Evidence