Diethyl Malonate → HCID 6994705, compound

Temperature

25 °C

At room temperature, a three-neck flask with internal thermometer, dropping funnel and stirrer was initially charged under protective nitrogen gas with 33.1 g of sodium methoxide (95% pure, 0.583 mol) in 250 ml of dry ethyl acetate. Subsequently, 97.5 g of diethyl malonate (0.609 mol) were added dropwise at from 20 to 30° C. The clear mixture was stirred at 25° C. for 30 min, and 85.7 g of (S)-1-methylbutyl methanesulfonate (0.516 mol) were added undiluted. The mixture was heated to 79° C. and stirred for 7 h. After cooling to 25° C., the suspension was admixed with 800 ml of methylene chloride and 500 ml of 5% by weight ammonium chloride solution. After phase separation, the organic phase was washed with 150 ml of water and then dried over sodium sulfate. After distillative removal of solvent, diethyl [(R)-1-methylbutyl]malonate was obtained in a yield of 105 g. The product contains dimethyl ester and ethyl methyl ester, formed by transesterification (GC purity: sum of Me/Me, Me/Et, Et/Et: 96%). The corrected yield is 96% of theory.

1. customAt room temperature, a three-neck flask with internal thermometer, dropping
2. temperatureThe mixture was heated to 79° C.
3. stirringstirred for 7 h
4. temperatureAfter cooling to 25° C.
5. customAfter phase separation
6. washthe organic phase was washed with 150 ml of water
7. dry with materialdried over sodium sulfate
8. customAfter distillative removal of solvent

ORD record

ord-6ebcf2cc5ee04f08a9c00c631040c44a

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07534908B2