Methyl Acrylate → HCID 86706689, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-bromo-5-methyl-2,3-dihydro-1H-inden-1-one (commercially available), 1.45 g, 6.42 mmol) and methyl acrylate (1.28 mL, 14.1 mmol) in 2-Me THF (6 mL) cooled to 0° C. was added potassium tert-butoxide (0.864 g, 7.70 mmol) in portions. After stirring for 2 h at r.t., water (9.0 mL) and potassium hydroxide (0.36 g, 6.42 mmol) were added and the mixture was heated at reflux overnight. The mixture was allowed to cool to r.t. and brine was added. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated to yield 1.38 g (70% yield) of the title compound: 1H NMR (500 MHz, CDCl3) δ ppm 1.86 (m, 2 H) 2.20 (m, 2 H) 2.45 (m, 2 H) 2.51 (s, 3 H) 2.71 (dt, 2 H) 3.13 (s, 2 H) 7.38 (s, 1 H) 7.95 (m, 1 H): MS (ES+) m/z 307, 309 [M+H]+.

Provenance & Evidence