Реакция #59932

Уравнение реакции

ethyl 3-oxopentanoate

ethylene glycol

triethyl orthoformate

p-toluenesulfonic acid monohydrate

→

title compound

Выход 58.9%

Ethyl(2-ethyl-1,3-dioxolan-2-yl)acetate

Выход 58.9%

Растворители

ethyl acetate

heptane

Условия реакции

Обработка

1. 1
   Промывкаwas washed with water
2. 2
   ПромывкаThe organic layer was washed with a saturated saline solution
3. 3
   Сушкаdried over magnesium sulfate
4. 4
   Фильтрацияfiltrated
5. 5
   Концентрированиеthe filtrate was concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in heptane
7. 7
   Промывкаsubjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/0→10/1)

Методика

A mixture of ethyl 3-oxopentanoate (5 g, 34.7 mmol), ethylene glycol (10.8 g, 174 mmol), triethyl orthoformate (5.14 g, 34.7 mmol), and p-toluenesulfonic acid monohydrate (598 mg, 3.14 mmol) was stirred at room temperature overnight. To the reaction mixture, heptane and ethyl acetate were added to dilute solution, which was washed with water. The organic layer was washed with a saturated saline solution, dried over magnesium sulfate, filtrated and the filtrate was concentrated under reduced pressure. The residue was dissolved in heptane and subjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/0→10/1) to obtain the title compound (3.85 g, yield: 58.9%) as colorless oil.

Источник