p-Toluenesulfonic acid → HCID 68109162, compound

Participants

Reaction Steps

To a solution of 4-iodobenzyl alcohol (2.0 g, 8.54 mmol) in dry dichloromethane (15 mL) was added 3,4-dihydro-2H-pyran (0.92 mL, 10.25 mmol) followed by p-toluenesulfonic acid (147 mg, 0.85 mmol). The reaction mixture was stirred at ambient temperature for 2 h under a nitrogen atmosphere before partitioning between water and dichloromethane. The organic layer was washed with water followed by brine solution then dried over Na2SO4. After concentration in vacuo the residue was purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate) to give 2-(4-iodobenzyloxy)tetrahydro-2H-pyran (2.0 g, 74%) as a colorless liquid: 1H NMR (CDCl3, 400 MHz) δ 8.12 (d, J=8.4 Hz, 2H), 7.12 (d, J=8.4 Hz, 2H), 4.76-4.65 (m, 2H), 4.46 (d, J=12.0 Hz, 1H), 3.94-3.84 (m, 1H), 3.59-3.49 (m, 1H), 1.91-1.49 (m, 6H).

Provenance & Evidence