4-Toluenesulfonyl chloride → 2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

Participants

Reaction Steps

2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolan (3.96 g, 30 mmol) and triethyl amine (5 mL) were dissolved in CH2Cl2 (50 mL). p-Toluenesulphonyl chloride (3.8 g, 20 mmol) was added. The solution was stirred for 3 h after which 4-dimethylaminopyridine (0.05 g, 0.04 mmol) was added. The solution was stirred for 0.5 h after which the solution was concentrated in vacuo. The residue was taken up in CH2Cl2 and the organic phase was washed with H2O, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography to afford the title compound.

Provenance & Evidence