반응 #1244273

반응 방정식

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

triethyl amine

tosyl chloride

→

white solid

수율 96.0%

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

수율 96.0%

용매

dichloromethane

반응 조건

후처리

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

실험 절차

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).

출처