Ethyl Acetate → HCID 69422514, compound

Participants

Reaction Steps

A solution of (2S)(4-Hydroxy-3-iodide-)-2-methoxy dihidrocinnamic acid (197 mg, 0.56 mmol), 4-methoxyphenyl boronic acid (170.7 mg, 1.12 mmol) and tetrakis(triphenylphosphine)-palladium (0) (8.7 mg, 0.5 mmol) in 11 mL of a mixture 20:1 toluene/ethanol together with 2 mL of a 2N Na2CO3 was heated to 120° for 16 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature and dilute with ethyl acetate (20 mL). It was washed with H2O (3×5 mL) and brine (3×5 mL). The combined organic layers were dried (MgSO4), filtered and concentrated under vacuum. The resultant crude was purified by column chromatography (silica gel, hexanes/ethyl acetate 8:2). Colorless oil (123 mg, 67%). 1H-NMR (200.15 MHz, CDCl3): δ 7.39 (dd, 2H, J=2.1, 6.4), 7.08–7.03 (m, 2H), 6.97 (dd, 2H, J=2.1, 6.7), 6.85 (dd, 1H, J=1.3, 7.5), 5.60 (s, 1H), 4.17 (q, 2H, J=7.0), 3.95 (dd, 1H, J=5.9, 6.4), 3.82 (s, 3H), 3.35 (s, 3H), 2.97 (d, 2H, J=6.4), 1.22 (t, 3H, J=7.2)

Provenance & Evidence