反应详情

温度

-78 °C

2-Phenyl-2,2-dimethylethylmagnesium bromide (10 mmol, 20 mL of 0.5 M solution in diethyl ether) was added to solution of diethyl oxalate (1.5 g, 10.5 mmol) in anhydrous THF (20 mL) cooled to −78° C. and maintained under argon. After 1 hour, TLC in hexanes-EtOAc (7:1) indicated most of the diethyl oxalate had been consumed. The reaction mixture was quenched with a saturated solution of ammonium chloride and extracted with three 50 mL portions of EtOAc. The combined extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to give a light brown, thick oil which was purified by flash column chromatography over silica gel eluting with 5% EtOAc in hexanes to yield 4-methyl-2-oxo-4-phenylpentanoic acid ethyl ester as a light yellow oil (1.1 g, 51%).

1. temperaturemaintained under argon
2. customhad been consumed
3. customThe reaction mixture was quenched with a saturated solution of ammonium chloride
4. extractionextracted with three 50 mL portions of EtOAc
5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo
7. customto give a light brown, thick oil which
8. customwas purified by flash column chromatography over silica gel eluting with 5% EtOAc in hexanes