3,4-dihydro-2H-pyran → HCID 58292840, compound

Participants

Reaction Steps

A solution of 2-bromo-4,6-dihydroxy-benzaldehyde (4.69 g, 21.7 mmol) in dichloromethane (100 mL) was treated with DHP (3.94 mL, 43.4 mmol) and PPTS (200 mg) at room temperature for 1 h. The reaction mixture was concentrated to dryness. The residue purified by flash column chromatography (silica, hexanes/ethyl acetate=4:1) to give the title compound (5.96 g, 92%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 12.2 (s, 1H), 10.1 (s, 1H), 6.88 (d, J=2.1 Hz, 1H), 6.58 (d, J=2.1 Hz, 1H), 5.56 (s, 1H), 3.84-3.81 (m, 1H), 3.68-3.62 (m, 1H), 1.96-1.54 (m, 6H).

Provenance & Evidence