3,4-dihydro-2H-pyran → 2-Hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde

Participants

Reaction Steps

To a mixture of 2,4-dihydroxy-6-methoxymethyl-benzaldehyde (2.62 g, 14.45 mmol) in dichloromethane (50 mL) was added 3,4-dihydro-2H-pyran (2.42 g mL, 28.90 mmol) and pyridium p-toluenesulfonic acid (0.050 g) at room temperature. The resulting mixture was stirred at room temperature for 16 hours then concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 2-hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (3.06 g, 80%). 1H NMR (400 MHz, CDCl3) δ 12.30 (s, 1H), 10.10 (s, 1H), 6.80 (s, 1H), 6.79 (s, 1H), 5.47 (s, 1H), 4.60 (s, 2H), 3.80 (m, 1H), 3.60 (m, 1H), 3.40 (s, 3H), 2.00-1.50 (m, 6H).

Provenance & Evidence