반응 #5485

반응 방정식

Cyclooctanone

Triethyloxonium tetrafluoroborate

Ethyl diazoacetate

→

2-ethoxycarbonyl-cyclononanone

용매

methylene chloride

반응 조건

후처리

1. 1
   기타The 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
   추출The reaction mixture is then extracted several times with methylene chloride
5. 5
   건조the combined organic layers are dried (Na2SO4)
6. 6
   기타the solvent is evaporated
7. 7
   workup.DISTILLATIONThe product is purified by vacuum distillation (0.2-1.0 mm Hg)
8. 8
   기타boiling between 100°-125° C.
9. 9
   기타is collected

실험 절차

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.

출처