Reaction #1244273

Reaction equation

2-phenyl-1,3-dioxan-5-ol

triethyl amine

tosyl chloride

→

white solid

Yield 96.0%

2-Phenyl-1,3-dioxan-5-yl 4-methylbenzenesulfonate

Yield 96.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONThe reaction was poured onto water (800 mL)
2. 2
   Extractionextracted into DCM
3. 3
   Concentrationconcentrated to dryness
4. 4
   OtherThe crude mixture was recrystallized from EtOAc

Procedure

To a 2 liter round bottom flask was added 2-phenyl-1,3-dioxan-5-ol (50 g, 277 mmol), triethyl amine (42.1 g, 416 mmol), DMAP (3.39 g, 27.7 mmol) and dichloromethane (1 L). The reaction was cooled to 0° C. To this solution was added tosyl chloride (58.2 g, 305 mmol) and the reaction was stirred overnight at RT. The reaction was poured onto water (800 mL) and extracted into DCM. The organic layers were combined and concentrated to dryness. The crude mixture was recrystallized from EtOAc:Hex to afford 88 g (96% yield) of a white solid. 1H NMR (CDCl3, 400 MHz), δ: 2.44 (3H, s), 4.09 (2H, dd, J=13.6, 2 Hz), 4.27 (2H, dd, J=13.6, 1.6 Hz), 4.51 (2H, pseudo t, J=1.6 Hz), 7.33-7.36 (5H, m), 7.44-7.45 (2H, m), 7.85 (2H, d, J=8.39 Hz). Mass Spec (lo-res): Calc'd for C17H18O5S: 334.09. found: 335.1 (M+H).

Source