Methyl Acrylate → HCID 86706719, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-((3,3-difluorocyclobutyl)methoxy)-2,3-dihydro-1H-inden-1-one (Intermediate 11, 7.0 g, 27.8 mmol) and methyl acrylate (5.51 mL, 61.1 mmol) in 2-Me THF (6 mL) was cooled to 0° C. and potassium tert-butoxide (3.74 g, 33.3 mmol) was added in portions. After stirring for 2 h at r.t., water (9 mL) and potassium hydroxide (1.56 g, 27.8 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, providing 3.51 g, 37% yield of the title compound. 1H NMR (500 MHz, CDCl3) ppm 1.80-1.91 (m, 2H) 2.17-2.26 (m, 2H) 2.39-2.57 (m, 4H) 2.58-2.82 (m, 5H) 3.16 (s, 2H) 4.05 (d, 2H) 7.20 (d, 1H) 7.25 (dd, 1H) 7.40 (d, 1H); MS (ES+) m/z 335 [M+H]+.

Provenance & Evidence