Triethylamine → 4-(3-Benzyloxy-phenoxy)-2-methoxymethoxy-6-methyl-benzaldehyde

Participants

Reaction Steps

A mixture of 4-hydroxy-2-methoxymethoxy-6-methyl-benzaldehyde (5.3 g, 27.2 mmol), 3-benzyloxyphenylboronic acid (9.3 g, 40.8 mmol), Cu(OAc)2 (4.9 g, 27.2 mmol), Et3N (18.9 mL, 135.9 mmol) and 4 Å molecular sieves (26 g) in DCM (150 mL) was stirred at room temperature for 12 hours. The reaction mixture was filtered through a pad of celite and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 4-(3-benzyloxy-phenoxy)-2-methoxymethoxy-6-methyl-benzaldehyde (3.5 g, 34%). 1H NMR (400 MHz, CDCl3): δ 10.55 (s, 1H), 7.43-7.25 (m, 6H), 6.82 (dd, J=2.0, 8.4 Hz, 1H), 6.69-6.66 (m, 3H), 6.37 (s, 1H), 5.21 (s, 2H), 5.04 (s, 2H), 3.49 (s, 3H), 2.52 (s, 3H). MS (ESI) m/z=379 [M+H]+.

Provenance & Evidence