Hydrochloric Acid → Diethyl 2-Propynylmalonate

Temperatur

80 °C

To a mixed solution of triethyl methanetricarboxylate sodium salt (25.0 g) in toluene/DMF (120 mL/120 mL) was added propargyl bromide (25.0 g), and the mixture was stirred at 80° C. for 1.5 hr. After allowing to cool, dilute hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate (60 mL). The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was dissolved in THF (30 mL), sodium ethoxide (7.60 g) was added, and the mixture was stirred at room temperature for 1 hr. 1 mol/L Hydrochloric acid (150 mL) was added, and the mixed solution was extracted with chloroform (100 mL). The organic layer was concentrated, and the residue was purified by silica gel column chromatography to give the title compound (35.0 g) as an oil.

1. temperatureto cool
2. extractionthe mixture was extracted with ethyl acetate (60 mL)
3. washThe organic layer was washed with saturated brine
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was dissolved in THF (30 mL)
6. additionsodium ethoxide (7.60 g) was added
7. stirringthe mixture was stirred at room temperature for 1 hr
8. addition1 mol/L Hydrochloric acid (150 mL) was added
9. extractionthe mixed solution was extracted with chloroform (100 mL)
10. concentrationThe organic layer was concentrated
11. customthe residue was purified by silica gel column chromatography

ORD-Eintrag

ord-94f6feb649894b42a6431cda4cc4f278

Quelldatensatz

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08461209B2