Hydrochloric Acid → Diethyl 2-(but-2-yn-1-yl)malonate

To a stirring mixture consisting of diethyl malonate (24.3 g, 141 mmol) in THF (140 mL) was added sodium hydride (60% dispersion in oil, 2.8 g, 70 mmol) and the resulting reaction mixture was stirred for 50 minutes. To the reaction mixture was added 1-bromobut-2-yne (GFS, 6.2 g, 47 mmol), and the mixture was stirred for two hours. The reaction mixture was treated carefully with 0.5 N HCl and extracted with ethyl acetate. The organic phase was washed with water, then brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography. Elution with ethyl acetate-heptane (5:95 to 15:85 v/v) afforded the title intermediate (11.5 g, quantitative yield) as a clear oil.

1. customthe resulting reaction mixture
2. stirringthe mixture was stirred for two hours
3. extractionextracted with ethyl acetate
4. washThe organic phase was washed with water
5. dry with materialbrine, dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by silica gel chromatography
9. washElution with ethyl acetate-heptane (5:95 to 15:85 v/v)

ORD record

ord-0a92896d03ba4b64a75442a0318c7817

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09180116B2