Triethylamine → HCID 39236853, compound

Participants

Reaction Steps

According to the method described in J. Org. Chem., 2009, 74, 929, bis(norbornadiene)rhodium tetrafluoroborate (0.22 g, 0.59 mmol) and (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.39 g, 0.62 mmol) were added to a mixture of 2-fluorophenylboronic acid (5.37 g, 38.4 mmol) in nitrogen sparged dioxane (30 mL) under nitrogen atmosphere. After 2 hours of agitation at ambient temperature, water was added (4.6 mL) followed by 2-cyclopenten-1-one (3.06 mL, 36.5 mmol) and triethylamine (5.09 g, 36.5 mmol). The agitation was continued for 24 h at 30° C. then the mixture was diluted with heptane (30 mL), MTBE (10 mL), and water (30 mL). The organic layer was separated and washed with water (50 mL). The aqueous layers were combined and extracted with MTBE/heptane (1:2, 50 mL). Combined organic extracts were dried (Na2SO4) and concentrated. Purification by chromatography (SiO2, hexane/20% ethyl acetate) afforded the title compound (3.94 g, 22.1 mmol, 61%). 1H NMR (300 MHZ, DMSO-d6) δ 7.46-7.27 (M, 1H), 7.25-7.05 (M, 3H), 3.56-3.26 (M, 1H), 2.22-1.41 (M, 6H). MS (ESI) m/z 177 (M−H)+.

Provenance & Evidence