Water → HCID 49834378, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-trifluoromethyl-phenyl]-propionic acid methyl ester (preparation 2) (4.6 mmol) and [(1,4-hydroquinone)-rhodium(COD)]BF4 (Son et al., J. Am. Chem. Soc. 2005, 127, 12238) (2 mol %) in water/dimethoxyethane (1:1, 20 mL, degassed) was added 2-cyclopenten-1-one (4.6 mmol) and LiOH (8 mol %). The mixture was warmed to 50° C. and stirred overnight. Additional water was added, and the mixture was extracted with dichloromethane. The organic phase was separated, dried and concentrated in vacuo to afford the title compound as a brown oil. 1H NMR (300 MHz, DMSO) δ 7.72-7.56 (m, 2H), 7.54-7.39 (m, 1H), 3.62 (s, 3H), 3.53-3.36 (m, 1H), 3.08-2.95 (m, 2H), 2.70-2.47 (m, 3H), 2.43-2.21 (m, 4H), 2.02-1.83 (m, 1H).

Provenance & Evidence