Furfural → HCID 68276449, compound

Participants

Reaction Steps

To a solution of 2-[(6-bromo-1-chloronaphthalen-2-yl)oxy]ethanaminium chloride (91 mg, 0.27 mmol) in 10 mL of MeOH, K2CO3 (41 mg, 0.30 mmol) was added. After 10 min, 45 μL (0.54 mmol) of furan-2-carbaldehyde were added. The resulting solution was stirred for 1 h at room temperature, added with sodium borohydride (10 mg, 0.27 mmol) and then stirred for further 2 h at room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 95:5) to afford 2-[(6-bromo-1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)ethanamine as a brown solid (87 mg, 85% yield). 1H-NMR (DMSO-d6) δ: 8.35 (1H, d, J=2.05 Hz), 8.07 (1H, d, J=9.01 Hz), 8.00 (1H, d, J=9.01 Hz), 7.81 (1H, dd, J=1.05 Hz, J=2.08 Hz), 7.78 (1H, dd, J=2.05 Hz, J=8.98 Hz), 7.67 (1H, d, J=8.98 Hz), 6.70 (1H, dd, J=1.05 Hz, J=3.34 Hz), 6.34 (1H, dd, J=2.08 Hz, J=3.34 Hz), 4.55 (2H, d, J=5.44 Hz), 4.43 (2H, s), 3.43 (2H, d, J=5.44 Hz). HPLC-MS (ESI+): m/z 381.21 [M+H+].

Provenance & Evidence