3,4-dihydro-2H-pyran → HCID 18469682, compound

Participants

Reaction Steps

To a solution of 2-bromo-5-hydroxymethylpyridine (4 Scheme 27, 7.3 g, 38.8 mmol) and 3,4-dihydro-2H-pyran (3.6 g, 42.7 mmol) in dichloromethane (150 mL) was added p-TsOH (200 mg) and the mixture was stirred for 5 h at room temperature. The reaction mixture was concentrated and purified by column chromatography (1:5 ethyl acetate/hexanes) to give the desired compound as a liquid (10 g, 95%); 1H NMR (300 MHz, CDCl3) δ 1.42-1.81 (6 H), 3.48 (m, 1 H), 3.80 (m, 1 H), 4.43 (m, 1 H), 4.62-4.73 (2 H), 7.42 (m, 1 H), 7.53 (m, 1 H), 8.30 (m, 1 H); 13C NMR (75 MHz, CDCl3) 19.5, 25.5, 30.6, 62.5, 65.8, 98.3, 128.0, 133.5, 138.4, 141.3, 149.7. HRMS (EI) calcd for C11H14BrNO2 271.0208 and 273.0187, found 271.0207 and 273.0171.

Provenance & Evidence