反応 #2460287

反応方程式

1,3-dicyclohexylcarbodiimide

2-butynoic acid

9-fluorenemethanol

dimethylamino-pyridine-p-toluenesulfonic acid salt

→

9-fluorenylmethyl 2-butynoate

収率 55.3%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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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