反応 #1244273

反応方程式

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

triethyl amine

tosyl chloride

→

white solid

収率 96.0%

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

収率 96.0%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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).

出典