Triethylamine → methyl 3-(4-nitrophenyl)prop-2-ynoate

1-Iodo-4-nitrobenzene (2.5 g, 10 mmol) was added to a solution of triethylamine (2.0 g, 20 mmol) in THF (40 mL). PdCl2 (PPh3)2 (0.14 g, 0.20 mmol), cuprous iodide (0.076 g, 0.40 mmol) and methyl propiolate (3.4 g, 40 mmol) were added and the resulting mixture was heated to reflux overnight. The reaction mixture was cooled to r.t., the solvent evaporated, and the crude compound dissolved in dichloromethane. The organics were filtered to remove insoluble material and the filtrate was washed with water, brine solution and dried over sodium sulfate. The filtrate was concentrated and the residue purified over silica gel using 15% ethyl acetate in petroleum ether as eluent to afford (4-nitrophenyl)-propynoic acid methyl ester (1.20 g, 59%) as a white solid.

1. temperaturethe resulting mixture was heated
2. temperatureto reflux overnight
3. customthe solvent evaporated
4. dissolutionthe crude compound dissolved in dichloromethane
5. filtrationThe organics were filtered
6. customto remove insoluble material
7. washthe filtrate was washed with water, brine solution
8. dry with materialdried over sodium sulfate
9. concentrationThe filtrate was concentrated
10. customthe residue purified over silica gel using 15% ethyl acetate in petroleum ether as eluent

ORD record

ord-9347f1837b394c75a7048578f063a0cc

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604029B2