Triethylamine → HCID 18329179, compound

Participants

Reaction Conditions

Reaction Steps

10.5 g (59 mmol) of methyl 3-(4-hydroxy-phenyl)-acrylate were dissolved in 170 ml of tetrahydrofuran and treated in succession with 9.1 ml (65 mmol) of triethylamine and 0.079 g (0.65 mmol) of 4-dimethylamino-pyridine (DMAP). 6.8 g (65 mmol) of methacryloyl chloride were added dropwise to the solution, cooled to about 15° C., over a period of minutes. The reaction batch was stirred at room temperature overnight and subsequently filtered over a thin silica gel layer. The silica gel layer was rinsed thoroughly with THF. After evaporation of the solvent the crude product was recrystallized from about 200 ml of ethanol. It was filtered off, dried and recrystallized once more from ethanol. Filtration and drying at 50° C. in a water-jet vacuum gave 10.3 g of 4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 2-methyl-acrylate as white crystals with a melting point of 76-80° C. and an absorption maximum of λmax. (in CH2Cl2)=281.7 nm (ε=24290 l/mol cm).

Provenance & Evidence