Diethyl Malonate → Propanedioic acid, (2-methyl-2-propenyl)-, dimethyl ester

To a solution of diethyl malonate (2.30 g) in THF (20 mL) was added 60% sodium hydride (592 mg) at 0° C., and the mixture was stirred for 1 hr. 3Bromo-2-methylpropene (2.00 g) was added to the reaction mixture, and the mixture was stirred at room temperature for 20 hr. Aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (2.60 g) as a colorless oil.

1. stirringthe mixture was stirred at room temperature for 20 hr
2. extractionthe mixture was extracted with ethyl acetate
3. washThe extract was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

ORD record

ord-ad693324676f4127bdfd577012ab2d27

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181186B2