Réaction #324625

Équation de réaction

3-methylbutane-1,3-diol

p-toluene-sulfonylchloride

→

title compound

3-Hydroxy-3-methylbutyl 4-methylbenzenesulfonate

Solvants

dichloromethane

pyridine

dichloromethane

Conditions de réaction

Traitement

1. 1
   Lavagewashed with 1 M aqueous HCl solution and brine
2. 2
   SéchageAfter drying (MgSO4) the solvent
3. 3
   Autreis evaporated
4. 4
   Autrethe product is purified by chromatography on silica gel (cyclohexane/ethyl acetate 90:10→70:30)

Mode opératoire

To a solution of 3-methylbutane-1,3-diol (2.5 mL) in dichloromethane (30 mL) and pyridine (2.1 mL) is added at 0° C. p-toluene-sulfonylchloride (4.6 g) in portions. The mixture is stirred for 12 hours at room temperature, diluted with dichloromethane and washed with 1 M aqueous HCl solution and brine. After drying (MgSO4) the solvent is evaporated and the product is purified by chromatography on silica gel (cyclohexane/ethyl acetate 90:10→70:30) to give the title compound. Yield: 3.2 g; Mass spectrum (ESI+): m/z=276 [M+NH4]+.

Source