Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 60102584, compound

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Reaction Steps

A solution of dibenzyl [3-(tetrahydro-2H-pyran-2-yloxy)propyl]phosphonate (3.08 g, 7.62 mmol) and pyridiniurn p-toluenesulfonate (0.191 g, 0.762 mmol) in EtOH (76 mL) was stirred at 55° C. overnight. The reaction mixture was cooled to room temperature and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 100% EtOAc in hexanes over 3096 mL, 100% EtOAc for 3888 mL) to afford dibenzyl (3-hydroxypropyl)phosphonate. Rf=0.34 (EtOAc). LCMS calc.=321.13; found=321.04 (M+H)+. 1H NMR (500 MHz, CHCl3): δ 7.35-7.28 (m, 10 H); 5.02 (dd, J=11.9, 8.9 Hz, 2 H); 4.94 (dd, J=11.9, 8.0 Hz, 2 H); 3.60 (t, J=5.6 Hz, 2 H); 3.37 (s, 1 H); 1.90-1.75 (m, 4 H).

Provenance & Evidence