Ethylene Glycol → HCID 21940676, compound

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. 5-Amino-1-pentanol (135 μL, 1.24 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, yellow-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 organic phase was dried (Na2SO4), concentrated, and the residue was purified by flash chromatography on silica gel (2×15 cm; ethyl acetate; 15 mL fractions). Fractions 6-15 provided 177 mg (85% yield) of the product as a pale tan oil. 1H NMR (400 MHz, CDCl3): δ 6.80-6.74 (m, 2H), 6.60-6.54 (m, 2H), 3.74 (s, 3H), 3.65 (t, J=6.4 Hz, 2H), 3.07 (t, J=7.0 Hz, 2H), 2.5 (br s, 2H), 1.68-1.55 (m, 4H), 1.52-1.41 (m, 2H). 13C NMR (100 MHz, CDCl3): δ 151.9, 142.6, 114.8, 114.0, 62.7, 55.8, 44.9, 32.4, 29.4, 23.3. IR (neat, cm−1): 3350, 1511, 1233, 1036, 820. Anal. Calcd. for C12H19NO2: C, 68.87; H, 9.15. Found: C, 68.93; H, 9.12.

Provenance & Evidence