Acetone cardice → (2-Ethyl-benzofuran-3-yl)-(2'-hydroxy-[1,1';3',1"]terphenyl-5'-yl)-methanone

Participants

Reaction Steps

At −78° C., to a stirred solution of (2-ethyl-benzofuran-3-yl)-(2′-methoxy-[1,1′;3′,1″]terphenyl-5′-yl)-methanone (1.07 g, 2.47 mmol) in CH2Cl2 (10.1 mL) was added dropwise 1M boron tribromide/ CH2Cl2 (5.2 mL). After the addition was complete, the dry ice/acetone bath was replaced with an ice water bath and the reaction was stirred for 72 h, eventually warming to ambient temperature. The reaction was carefully quenched with crushed ice, diluted with H2O (16 mL) and extracted with ether. The ethereal extracts were dried (MgSO4) and concentrated. Purification on Biotage KP-Sil eluting with 15% acetone/hexane gave 0.86 g, (83%) of the title compound as a white solid, mp 142-143° C. 1H NMR (DMSO-d6) δ1.24 (t, 3H), 2.90 (quartet, 2H), 7.28-7.66 (m, 16H), 9.37 (s, 1H). IR (KBr) 3200, 2950, 1625, 1560 and 1175 cm−1. mass spectrum (EI), m/z 418 (M+). Anal. Calcd. for C29H22O3.0.35H2O: C, 82.00; H, 5.39; N, 0.00. Found: C, 82.06; H, 5.40; N, 0.07.

Provenance & Evidence