Chloroform → 4-(4-Methoxyphenyl)morpholine

Participants

Reaction Steps

According to General Procedure B, a mixture of 4-bromoanisole (63 μL, 0.50 mmol), morpholine (52 μL, 0.60 mmol), NaOt-Bu (67 mg, 0.70 mmol), Pd2(dba)3.CHCl3 (10 mg, 0.01 mmol), and 12f (8 mg, 0.02 mmol) in PhMe (2.5 mL) was heated, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (2:50:48 Et3N/Et2O/hexane, silica gel) gave 52e (64 mg, 67%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 6.92-6.84 (m, 4H), 3.86 (t, 4H, J=4.8 Hz), 3.77 (s, 3H), 3.06 (t, 4H, J=4.8 Hz); 13C NMR (75.5 MHz, CDCl3) δ 153.9, 145.5, 117.7, 114.4, 66.9, 55.5, 50.7.

Provenance & Evidence