反応 #515187

反応方程式

Magnesium

bromoethane

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

diethyl oxalate

→

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

収率 77.3%

溶媒

tetrahydrofuran

tetrahydrofuran

water

反応条件

後処理

1. 1
   温度cooled to −78° C
2. 2
   workup.STIRRINGAfter stirring for 1 hour at −78° C.
3. 3
   抽出The mixture was extracted with ether
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   その他The solvent was evaporated
6. 6
   その他the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1)

実験手順

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.

出典