Acetic Acid → HCID 21914447, compound

Participants

Reaction Steps

To a solution of 4-bromobenzaldehyde (616 mg, 3.3 mmol) in dichloroethane (50 mL) was added homomorpholine hydrochloride (548 mg, 4 mmol) and acetic acid (0.1 mL). Sodium triacetoxyborohydride (3.4 g, 16 mmol) was added and the reaction was stirred overnight. The reaction was quenched with sat. NH4Cl (30 mL). Ethyl acetate (250 mL) was added and the solution was washed with sat. NaHCO3 (2×50 mL), brine (50 mL), dried over MgSO4 and concentrated to dryness. The residue was flushed through a silica plug with (5% MeOH/CH2Cl2) to give a white solid (850 mg, 85%). 1H NMR (400 MHz, CDCl3) δ 7.28 (d, J=7.3 Hz, 2H), 7.10 (d, J=7.3 Hz, 2H), 3.66-3.57 (m, 2H), 3.55-3.50 (m, 2H), 3.46-3.42 (m, 2H), 3.16-3.10 (m, 2H), 2.55-2.45 (m, 4H), 1.75-1.65 (m, 2H).

Provenance & Evidence