Ethylene Glycol → p-Anisidine, N-cyclohexyl-

Participants

Reaction Conditions

Reaction Steps

An oven-dried resealable 15 mL Schlenk tube was charged with CuI (9.5 mg, 0.0499 mmol, 5.0 mol %), K3PO4 (440 mg, 2.07 mmol), evacuated and backfilled with argon. Cyclohexylamine (144 μL, 1.26 mmol), ethylene glycol (0.11 mL, 1.97 mmol), and a solution of 4-iodoanisole (235 mg, 1.00 mmol) in 1-butanol (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred magnetically at 100° C. for 14 h. The resulting thick, green-brown suspension was allowed to reach room temperature, poured into a solution of 30% aq ammonia (1 mL) in water (20 mL), and extracted with 3×15 mL of CH2Cl2. The colorless organic phase was dried (Na2SO4), concentrated, and the residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 5:1; 15 mL fractions). Fractions 9-17 provided 143 mg (70% yield) of the product as white crystals. 1H NMR (400 MHz, CDCl3): δ 6.79-6.72 (m, 2H), 6.60-6.53 (m, 2H), 3.74 (s, 3H), 3.22 (br s, 1H), 3.16 (tt, J=10.2, 3.6 Hz, 1H), 2.10-1.98 (m, 2H), 1.80-1.69 (m, 2H), 1.68-1.58 (m, 1H), 1.40-1.04 (m, 5H). 13C NMR (100 MHz, CDCl3): δ 151.8, 141.6, 114.8, 114.7, 55.8, 52.7, 33.6, 25.9, 25.0. IR (neat, cm−1): 3388, 1509, 1239, 1038, 818. Anal. Calcd. for C13H19NO: C, 76.06; H, 9.33. Found: C, 76.00; H, 9.32.

Provenance & Evidence