反应 #2460287

反应方程式

1,3-dicyclohexylcarbodiimide

2-butynoic acid

9-fluorenemethanol

dimethylamino-pyridine-p-toluenesulfonic acid salt

→

9-fluorenylmethyl 2-butynoate

收率 55.3%

溶剂

dichloromethane

反应条件

后处理

1. 1
   其他First, 9-fluorenylmethyl 2-butynoate was prepared
2. 2
   温度the reaction mixture was warmed to ambient and
3. 3
   过滤The urea by product was filtered
4. 4
   洗涤the filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine
5. 5
   干燥The solution was dried (Na2SO4)
6. 6
   浓缩concentrated
7. 7
   其他The product was purified by column chromatography

实验过程

First, 9-fluorenylmethyl 2-butynoate was prepared. A mixture of 2-butynoic acid (11.6 g, 138 mmol), 9-fluorenemethanol (35.2 g, 179 mmol), dimethylamino-pyridine-p-toluenesulfonic acid salt (16.3 g, 55 mmol), and anhydrous dichloromethane (210 mL) was cooled to 0° C. under nitrogen, and 1,3-dicyclohexylcarbodiimide (34.2 g, 166 mmol) was added. After 15 min, the reaction mixture was warmed to ambient and stirred for 12 h. The urea by product was filtered, and the filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine. The solution was dried (Na2SO4) and concentrated to deposit a yellow oil. The product was purified by column chromatography to provide 20.0 g (54% of theory) of 9-fluorenylmethyl 2-butynoate as a yellow-green solid. 1H NMR (CDCl3): δ 1.98 (s, 3H), 4.20 (m, 1H), 4.45 (d, 2H), 7.32 (m, 4H), 7.60 (d, 2H), 7.70 (d, 2H).

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