Sodium hydride → Diethyl 2-(3-(2-chlorophenyl)allyl)-2-(prop-2-yn-1-yl)malonate

Temperature

0 °C

An oven-dried, 100 mL three-necked round-bottomed flask under a nitrogen atmosphere was charged with diethyl 2-(prop-2-yn-1-yl)malonate S13 (1.8 g, 9.1 mmol), (E)-1-(3-bromoprop-1-en-1-yl)-2-chlorobenzene S14 (2.1 g, 11.0 mmol), and THF (60 mL). The solution was cooled to 0° C. in an ice bath for 15 min, then NaH (0.43 g of a 60% dispersion in mineral oil, 11.0 mmol) was added in one portion. The solution was stirred at 0° C. for 2 h. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 0.5:9.5). The reaction was then quenched with sat'd aq ammonium chloride solution (70 mL). The layers were separated and the aqueous phase was extracted with AcOEt (3×50 mL). The combined organic layers were dried over Na2SO4, gravity filtered, and concentrated under reduced pressure. The reaction residue was purified by silica gel flash chromatography, eluting with AcOEt/n-hexane 0.5:9.5, to provide 2.55 g of the title compound as a yellow oil in 81% yield.

1. customThe consumption of the starting material
2. customThe reaction was then quenched with sat'd aq ammonium chloride solution (70 mL)
3. customThe layers were separated
4. extractionthe aqueous phase was extracted with AcOEt (3×50 mL)
5. dry with materialThe combined organic layers were dried over Na2SO4, gravity
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe reaction residue was purified by silica gel flash chromatography
9. washeluting with AcOEt/n-hexane 0.5:9.5

ORD record

ord-26c19e8ce2a24e1fba1967b10a71faa7

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133234B2