Реакция #2460287

Уравнение реакции

1,3-dicyclohexylcarbodiimide

2-butynoic acid

9-fluorenemethanol

dimethylamino-pyridine-p-toluenesulfonic acid salt

→

9-fluorenylmethyl 2-butynoate

Выход 55.3%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеFirst, 9-fluorenylmethyl 2-butynoate was prepared
2. 2
   Температураthe reaction mixture was warmed to ambient and
3. 3
   ФильтрацияThe urea by product was filtered
4. 4
   Промывкаthe filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine
5. 5
   СушкаThe solution was dried (Na2SO4)
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe product was purified by column chromatography

Методика

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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