Hydrochloric Acid → 1,3-Diethyl 2-(1-oxopropyl)propanedioate

To magnesium chloride (2.96 g, 31.2 mmol) was added dry acetonitrile (5 mL) and the mixture was then cooled in ice and treated with diethyl malonate (5 g, 31.2 mmol). Once the mixture was cold, triethylamine (8.6 mL, 62.5 mmol) was added and the resulting suspension was stirred for 15 mins. Propionyl chloride (2.71 mL, 31.2 mmol) was added dropwise and the mixture was stirred at 0° C. for 1.5 h and at ambient temperature for 5 h. The mixture was cooled in an ice-bath and treated with aqueous hydrochloric acid (2M, 10 mL) and the product extracted with ether. The organic phase was washed with water then brine, dried and evaporated to afford 6.31 g of a yellow oil. This was dissolved in ether and washed with aqueous hydrochloric acid (2M) then brine, dried and evaporated to afford 5.93 g of the title compound.

1. temperaturethe mixture was then cooled in ice
2. stirringthe mixture was stirred at 0° C. for 1.5 h and at ambient temperature for 5 h
3. temperatureThe mixture was cooled in an ice-bath
4. extractionthe product extracted with ether
5. washThe organic phase was washed with water
6. dry with materialbrine, dried
7. customevaporated

ORD record

ord-537eb383344646faae936ee4b77179a1

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071588B2