反应 #6718

反应方程式

alcohol

6-{2-[2-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester

Triethylamine

methanesulfonyl chloride

→

compound 20

收率 85.4%

6-{2-[2-(2-{2-[2-(2-methylsulfonylethoxy)ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester

收率 85.4%

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度the mixture was chilled in an ice bath
2. 2
   workup.WAITat room temperature for two hours
3. 3
   过滤The reaction mixture was filtered through silica gel
4. 4
   其他to remove the triethylammonium chloride
5. 5
   洗涤the filtrate was washed successively with water, saturated NaHCO3, water and brine
6. 6
   干燥The organics were dried over Na2SO4
7. 7
   过滤filtered
8. 8
   浓缩concentrated in vacuo
9. 9
   其他The residue was purified by column chromatography (silica gel, 9/1 ethyl acetate/methanol)

实验过程

The non-polydispersed alcohol 19 (0.835 g, 1.97 mmol) was dissolved in 3.5 ml dry dichloromethane and placed under a nitrogen atmosphere. Triethylamine (0.301 ml, 0.219 g, 2.16 mmol) was added and the mixture was chilled in an ice bath. After two minutes, the methanesulfonyl chloride (0.16 ml, 0.248 g, 2.16 mmol) was added. The mixture was stirred for 15 minutes at 0° C., then at room temperature for two hours. The reaction mixture was filtered through silica gel to remove the triethylammonium chloride, and the filtrate was washed successively with water, saturated NaHCO3, water and brine. The organics were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 9/1 ethyl acetate/methanol) to give non-polydispersed compound 20 as a clear oil (0.819 g, 83%). FAB MS: m/e 503 (M+H).

来源