反应 #1244273

反应方程式

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

triethyl amine

tosyl chloride

→

white solid

收率 96.0%

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

收率 96.0%

溶剂

dichloromethane

反应条件

后处理

1. 1
   workup.ADDITIONThe reaction was poured onto water (800 mL)
2. 2
   萃取extracted into DCM
3. 3
   浓缩concentrated to dryness
4. 4
   其他The crude mixture was recrystallized from EtOAc

实验过程

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).

来源