Reaktion #515187

Reaktionsgleichung

Magnesium

bromoethane

1-bromo-2-(tetrahydropyran-2-yloxymethyl)benzene

diethyl oxalate

→

ethyl 2-oxo-2-[2-(tetrahydropyran-2-yloxymethyl)phenyl]acetate

Ausbeute 77.3%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to −78° C
2. 2
   workup.STIRRINGAfter stirring for 1 hour at −78° C.
3. 3
   ExtraktionThe mixture was extracted with ether
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   SonstigeThe solvent was evaporated
6. 6
   Sonstigethe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1)

Vorschrift

Magnesium (2.67 g, 0.110 mol) and bromoethane (0.20 ml) were added to a solution of 1-bromo-2-(tetrahydropyran-2-yloxymethyl)benzene (27.11 g, 0.100 mol) in tetrahydrofuran (50 ml) under an atmosphere of nitrogen, and the mixture was stirred at room temperature for 1 hour to prepare a Grignard reagent. The Grignard reagent was added dropwise to a solution of diethyl oxalate (29.23 g, 0.200 mol) in tetrahydrofuran (100 ml) cooled to −78° C. After stirring for 1 hour at −78° C., water (150 ml) was added. The mixture was extracted with ether, dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1) to give the desired compound ethyl 2-oxo-2-[2-(tetrahydropyran-2-yloxymethyl)phenyl]acetate (22.60 g, 77.3%) as an oil.

Quelle