p-Toluenesulfonic acid → HCID 11119203, compound

Participants

Reaction Steps

2-Bromopyridine-6-methanol (prepared as described in Tetrahedron Lett., 1996, 50, 2537) (5 g, 26.5 mmol) was added to a solution of dihydropyran (2.65 ml, 29.2 mmol), and p-toluenesulfonic acid (506 mg, 2.7 mmol) in dichloromethane (150 ml) at room temperature under nitrogen. After 24 h, the mixture was washed with sodium carbonate solution (×1) and water (×1), dried (MgSO4), evaporated in vacuo and the residue flash chromatographed on silica gel, eluting with 10% ethyl acetate/hexane to give the title-compound (6.04 g, 84%), 1H NMR (250 MHz, CDCl3) δ 1.5-1.9 (6H, m, 3 of CH2), 3.56 (1H, m, CH2O), 3.88 (1H, m, CH2O), 4.62 (1H, d, J=14.2 Hz, CH2O), 4.76 (1H, t, J=3.4 Hz, CHO), 4.93 (1H, d, J=14.6 Hz, CH2O), 7.37 (1H, d, J=7.6 Hz, Ar—H), 7.46 (1H, d, J=6.6 Hz, Ar—H), 7.56 (1H, t, J=7.6 Hz, Ar—H); MS (ES30) m/e 272 [MH]+.

Provenance & Evidence