Tetrahydrofuran → HCID 89601123, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 2-(4-bromo-2-chloro-6-methoxy-phenyl)-3-methoxy-5-prop-2-ynyl-cyclopent-2-en-1-one (0.147 g, 0.398 mmol), but-2-ynoic acid (0.0368 g, 0.437 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.0141 g, 0.0199 mmol) and 1,4-bis-(diphenylphosphino)butane (0.0170 g, 0.0398 mmol) was sealed and dimethyl sulfoxide (2 mL) was added via syringe followed by tetrabutylammonium fluoride (1 mol/L) in tetrahydrofuran (0.795 mL, 0.795 mmol) and then the solution was heated under microwave irradiation at 110°C. for 40 minutes. The reaction was cooled to room temperature, poured into water (20 ml) and diluted with EtOAc (10 ml). The phases were separated and the aqueous phase was extracted into ethyl acetate (2×10 ml). The combined organic extracts were washed with brine (10 ml), dried over MgSO4, filtered and evaporated to dryness under reduced pressure to give a yellow gum, 230 mg. The residue was dissolved in dichloromethane, adsorbed onto silica and purified by flash chromatography over silica using an EtOAc/isohexane gradient to give the desired compound as a yellow gum (42 mg, 32%) as a seperable mixture of atropisomers with identical spectral data. 1H NMR (400 MHz, CDCl3) δ ppm 7.09 (s, 1H), 6.82 (s, 1H), 3.77 (s, 3H), 3.64 (s, 3H), 3.11-3.09 (m, 1H), 2.74-2.51 (m, 4H), 2.05 (s, 3H), 1.99 (s, 1H).

Provenance & Evidence