Dimethyl oxalate → HCID 58365459, compound

To a mixture of 1-(2,2,5-trimethyl-1,3-dioxane5-yl)ethanone (0.76 g, 4.4 mmol) and THF (7.6 mL) was added sodium hydride (0.16 g, 6.6 mmol) under nitrogen atmosphere, and the resulting mixture was stirred at room temperature for 0.5 hour. To the resulting reaction mixture was added dimethyl oxalate (0.78 g, 6.6 mmol) and the mixture was heated at reflux for 2 hours. After the reaction was completed, saturated ammonium chloride aqueous solution was added to mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (ethyl acetate/n-hexane) to give methyl 2,4-dioxo-4-(2,2,5-trimethyl-1,3-dioxane5-yl)butanoate (1.0 g, yield: 88%) as colorless oil.

1. customTo the resulting reaction mixture
2. temperaturethe mixture was heated
3. temperatureat reflux for 2 hours
4. extractionthe resulting mixture was extracted with ethyl acetate
5. washThe extract was washed with brine
6. dry with materialdried over anhydrous sodium sulphate
7. concentrationconcentrated in vacuo
8. customThe resulting residue was purified on a silica gel column chromatography (ethyl acetate/n-hexane)

ORD record

ord-356e34888dfe483c801c8863e84ec142

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575197B2