تفاعل #5485

معادلة التفاعل

Cyclooctanone

Triethyloxonium tetrafluoroborate

Ethyl diazoacetate

→

2-ethoxycarbonyl-cyclononanone

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىThe 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
   استخلاصThe reaction mixture is then extracted several times with methylene chloride
5. 5
   تجفيفthe combined organic layers are dried (Na2SO4)
6. 6
   أخرىthe solvent is evaporated
7. 7
   workup.DISTILLATIONThe product is purified by vacuum distillation (0.2-1.0 mm Hg)
8. 8
   أخرىboiling between 100°-125° C.
9. 9
   أخرىis collected

الإجراء التجريبي

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.

المصدر