反応 #50239

反応方程式

Cyclooctanone

Triethyloxonium tetrafluoroborate

Ethyl diazoacetate

→

2-ethoxycarbonyl-cyclononanone

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他The reaction is quenched
2. 2
   workup.ADDITIONby pouring into a solution of sodium bicarbonate (160 g) in water (1.6 L)
3. 3
   workup.STIRRINGstirring overnight
4. 4
   抽出The reaction mixture is then extracted several times with methylene chloride
5. 5
   乾燥the combined organic layers are dried (Na2SO4)
6. 6
   その他the solvent is evaporated
7. 7
   workup.DISTILLATIONThe product is purified by vacuum distillation (0.2-1.0 mm Hg)
8. 8
   その他boiling between 100°-125° C.
9. 9
   その他is collected

実験手順

Cyclooctanone (25 g, 198 mmol) is dissolved in methylene chloride (500 mL) and the solution is cooled to 0° C. Triethyloxonium tetrafluoroborate (121.6 g, 640 mmol) is added. Ethyl diazoacetate (41.61 g, 365 mmol) is then added dropwise over 25 minutes, and the reaction is stirred at 0° C. for 4 hours. The reaction is quenched by pouring into a solution of sodium bicarbonate (160 g) in water (1.6 L) and stirring overnight. The reaction mixture is then extracted several times with methylene chloride, the combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by vacuum distillation (0.2-1.0 mm Hg) and the fraction boiling between 100°-125° C. is collected to give 2-ethoxycarbonyl-cyclononanone.

出典