Ethyl Acetate → HCID 69203662, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Pd(OAc)2 (67 mg, 0.30 mmol) in DMF (1 ml) was added to a stirred suspension of 4-(3,5-dimethoxyphenyl)-but-3-en-2-one (2.05 g, 9.96 mmol), 4-bromo-1,2-dimethoxybenzene (2.15 ml, 14.94 mmol), NaOAc (1.39 g, 16.94 mmol), and tetrabutylammonium bromide (3.53 g, 10.96 mmol) in DMF (19 ml). The suspension was heated at ˜60° C. overnight. The mixture was then poured into EtOAc (50 ml) and H2O (150 ml), followed by extraction with EtOAc (2×50 ml), washing with H2O (2×50 ml), brine (50 ml) and drying over MgSO4. The crude was purified flash column chromatography (10% EtOAc in hexane gradient to 25% EtOAc in hexane) to give 4-(3,4-dimethoxy-phenyl)-4-(3,5-dimethoxy-phenyl)-but-3-en-2-one as a gummy oil (0.49 g, 15%): 1HNMR (CDCl3) δ 6.93-6.92 (m, 1H, Ar), 6.82-6.77 (m, 2H, Ar), 6.53-6.51 (m, 2H, Ar and double bond proton), 6.38 (d, J=2 Hz, 2H, Ar), 3.87 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 3.79 (s, 6H, 2OCH3), 1.91 (s, 3H, CH3); 13C NMR (CDCl3) δ 160.9, 153.8, 150.7, 148.9, 141.1, 132.9, 126.5, 122.4, 113.2, 110.8, 100.9, 56.1, 55.8, 55.6, 55.4, 30.0; Anal. Calcd. For C20H22O5: C, 70.16; H, 6.48. Found: C, 70.26; H, 6.37; N, <0.05.

Provenance & Evidence