反应 #312603

反应方程式

hydroxyl-sulfonamide

4-(Benzyloxy)-3-hydroxybutane-1-sulfonamide

Tosyl chloride

water

→

sulfonate

收率 62.9%

1-(Benzyloxy)-4-sulfamoylbutan-2-yl 4-methylbenzenesulfonate

收率 62.9%

溶剂

pyridine

反应条件

后处理

1. 1
   温度maintaining the internal temperature below 10° C
2. 2
   其他The completed reaction
3. 3
   其他to give an orange solution which
4. 4
   萃取was extracted with iPrOAc/MTBE (1:1, 2×1.5L)
5. 5
   洗涤The combined organics were washed with brine (2×500 mL), aqueous HCL (2M, 2×500 mL)
6. 6
   干燥The organic portion was dried (Na2SO4)
7. 7
   过滤filtered
8. 8
   其他evaporated

实验过程

A solution of hydroxyl-sulfonamide 5 (77 g, 0.30 mol) in pyridine (730 mL, 9.5 vol) was cooled to <10° C. in a 2 L round bottom flask. Tosyl chloride (56.6 g, 0.30 mol) is added to the solution over 5 minutes maintaining the internal temperature below 10° C. The reaction was allowed to warm to room temperature with stirring overnight. The completed reaction was poured into water (10 vol, 770 mL) to give an orange solution which was extracted with iPrOAc/MTBE (1:1, 2×1.5L). The combined organics were washed with brine (2×500 mL), aqueous HCL (2M, 2×500 mL) then brine (1×500 mL). The organic portion was dried (Na2SO4), filtered and evaporated to give sulfonate 6 as an orange oil (78 g).

来源