반응 #2460287

반응 방정식

1,3-dicyclohexylcarbodiimide

2-butynoic acid

9-fluorenemethanol

dimethylamino-pyridine-p-toluenesulfonic acid salt

→

9-fluorenylmethyl 2-butynoate

수율 55.3%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타First, 9-fluorenylmethyl 2-butynoate was prepared
2. 2
   온도the reaction mixture was warmed to ambient and
3. 3
   여과The urea by product was filtered
4. 4
   세척the filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine
5. 5
   건조The solution was dried (Na2SO4)
6. 6
   농축concentrated
7. 7
   기타The product was purified by column chromatography

실험 절차

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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