4-Toluenesulfonyl chloride → HCID 51900550, compound

Participants

Reaction Steps

To a solution of 2.18 g (18.75 mmol) of (2S)-oxan-2-ylmethanol in pyridine (25 mL) are added 7.15 g (37.5 mmol) of p-toluenesulfonylchloride portionwise at 10° C. After complete addition the reaction is allowed to warm to room temperature and stirred for 18 h. The reaction is poured onto a stirred mixture of 6M aqueous HCl/ice. The mixture is extracted with DCM (3×25 mL). The organic layer is dried (MgSO4), filtered and the filtrate is concentrated under reduced pressure to give 3.91 g of (2S)-oxan-2-ylmethyl 4-methylbenzene-1-sulfonate. Yield: 76%, ES-MS: m/z: 293 [M+Na]; 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.21-1.32 (1H, m), 1.41-1.60 (4H, m), 1.80-1.90 (1H, m), 2.45 (3H, s), 3.37 (1H, td, J=11.41, 2.82 Hz), 3.48-3.58 (1H, m), 3.89-3.98 (3H, m), 7.34 (2H, d, J=8.09 Hz), 7.80 (2H, d, J=8.24 Hz).

Provenance & Evidence