Reaktion #59932

Reaktionsgleichung

ethyl 3-oxopentanoate

ethylene glycol

triethyl orthoformate

p-toluenesulfonic acid monohydrate

→

title compound

Ausbeute 58.9%

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

Ausbeute 58.9%

Lösungsmittel

ethyl acetate

heptane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle