反应详情

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.

1. temperaturecooled to −78° C
2. stirringAfter stirring for 1 hour at −78° C.
3. extractionThe mixture was extracted with ether
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was evaporated
6. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1)