Sodium Hydroxide → HCID 178482622, compound

Participants

Reaction Conditions

Reaction Steps

Racemic iodide 12i (89 mg, 0.25 mmol), PhB(OH)2 (34 mg, 0.28 mmol) and Pd(PPh3)4 (29 mg, 2.51×10−2 mmol) were added to a dry Schlenk flask, followed by dimethoxyethane (DME, 2 mL) and an aqueous solution of 3 M NaOH (0.17 mL, 0.50 mmol). Argon was bubbled through the resulting mixture for 10 minutes, and the system was heated at 55° C. for 14 h. The reaction was allowed to cool to room temperature, diluted with Et2O, washed with water (1×5 mL), brine (1×5 mL), dried over Na2SO4, filtered, and all volatiles were removed in vacuo. Flash column chromatography (silica gel, 98:2 hexane/EtOAc) afforded 55 (61 mg, 80%) as an orange oil: Rf 0.45 (90:10 hex/EtOAc); IR (KBr, CHCl3) vmax 3091, 2941, 2852, 2779, 1601, 1491, 1444, 1416 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.80-7.74 (m, 2H), 7.36-7.19 (m, 3H), 4.28-4.25 (m, 1H), 4.18 (s, 5H), 4.15-4.11 (m, 1H), 4.05 (t, 1H, J=2.7 Hz), 2.53 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 139.1, 128.4, 127.8, 125.9, 112.5, 78.1, 69.2, 66.5, 62.4, 58.0, 44.6; EIMS [m/z (%)] 305 (M+, 100); HRMS (EI) calcd for C18H19N56Fe: 305.0867. Found 305.0864.

Provenance & Evidence