Triethylamine → HCID 54268649, compound

Participants

Reaction Steps

A mixture of 1.38 g (5 mmol) of 6-iodo-3-hydroxyisobenzofuranone, 0.74 g (5.5 mmol) of p-methoxystyrene, 0.83 ml (5.5 mmol) Et3N, 0.01 g of Pd (OAc)2 and 1 ml of DMSO was prepared in a 10 ml flask. The flask was surmounted with a reflux condenser and the solution was heated to 95° (oil bath) with stirring under N2 for 1 hour. The dark solution was allowed to cool to RT and poured onto 75 ml of ice/H2O with stirring. After standing overnight, the solid which had formed was collected, washed well with cold H2O and air dried. It was then heated with 50 ml of 95% EtOH, charcoaled and filtered. The reddish filtrate was cooled in ice and deposited 100 mg of reddish-brown solid which was found to be impurity and was discarded. The filtrate was evaporated at reduced pressure and the residual orange-yellow solid was triturated with 25 ml of Et2O and filtered to afford 860 mg (60.9%) of the desired coupling product as a yellow solid; homogeneous by TLC--used as is for the next reaction.

Provenance & Evidence