HCID 59829157, compound → HCID 59829145, compound

Participants

Reaction Steps

To a stirred solution of 3,5-dibromo-4-(4-methoxybenzyloxy)benzaldehyde (C) (3.04 g, 7.60 mmol) in anhydrous THF (40 mL) under nitrogen, cooled to −76° C., was added dropwise over 15 min vinylmagnesium bromide (1.0 M solution in THF, 11.4 mL, 11.4 mmol), keeping the internal temperature below −70° C. The mixture was stirred at <−70° C. for 65 min, and then quenched with saturated aqueous ammonium chloride solution (6 mL). The stirred mixture was allowed to warm to room temperature, and then partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was washed with saturated aqueous sodium chloride (80 mL), dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (silica gel, 15% EtOAc/pet. ether) to give 2.45 g (75%) of the title compound as a colourless oil. 1H NMR δ (ppm) (CDCl3): 1.96 (1 H, d, J=3.75 Hz), 3.83 (3 H, s), 4.96 (2 H, s), 5.14 (1 H, t, J=4.58 Hz), 5.27 (1 H, d, J=10.29 Hz), 5.35-5.42 (1 H, m), 5.98 (1 H, ddd, J=17.08, 10.28, 6.28 Hz), 6.90-6.96 (2 H, m), 7.50-7.57 (4 H, m).

Provenance & Evidence