2-(2-Hydroxyethyl)pyridine → 2-Hydroxy-3-[2-(2-pyridinyl)ethoxy]benzaldehyde

Participants

Reaction Steps

2-benzyloxy-3-hydroxy-benzaldehyde 16 (0.30 g, 1.3 mmol), triphenylphosphine (0.41 g, 1.6 mmol) and 2-(2-hydroxyethyl)pyridine (0.18 ml, 1.6 mmol) were stirred in THF (15 ml), followed by the addition of DEAD (0.25 ml, 1.6 mmol). After stirring for 12 h, the reaction mixture is partitioned between ethyl acetate (200 ml) and saturated aqueous sodium hydrogen carbonate (200 ml). The organic layer is separated, dried (MgSO4), filtered and concentrated to give a brown oil. The brown oil is purified by flash chromatography (50% ethyl acetate/hexanes) to afford 0.29 g (66%) of 2-hydroxy-3-(2-pyridin-2-ylethoxy)benzaldehyde 17 as a light yellow solid.

Provenance & Evidence