Water → 2-Allyloxy-5-methoxybenzylamine

Participants

Reaction Steps

Step AS (4). To a solution of 2-allyloxy-5-methoxybenzyl azide (4.5 g, 21 mmol) in 150 mL of anhydrous THF was added triphenylphosphine (10.8 g, 41 mmol) and 0.5 mL of water. The mixture was stirred at rt for 7 h. The reaction was concentrated under vacuum and the residue was partitioned between Et2O and 2 N HCl. The aqueous layer was basified with 2 N NaOH to pH 10 and extracted with EtOAc (3×40 mL). The organic layers were combined and washed with brine then dried over magnesium sulfate. After concentration, the residue was purified by silica gel chromatography, eluting with a mixture of 30% 2N ammonia in methanol and 70% EtOAc to yield 2-allyloxy-5-methoxybenzylamine as colorless oil (2.2 g, 55%). LC-MS (M+H)+=194; 1H NMR (400 MHz, CD3OD) δ ppm 3.75 (s, 3H) 4.08 (s, 2H) 4.60 (d, J=5.29 Hz, 2H) 5.22-5.30 (m, J=10.58 Hz, 1H) 5.35-5.44 (m, J=17.37 Hz, 1H) 6.01-6.15 (m, 1H) 6.89-6.96 (m, 2H) 6.96-7.02 (m, 1H).

Provenance & Evidence