HCID 19748779, compound → HCID 19748798, compound

Participants

Reaction Steps

In a 1 L 3-necked flask equipped with a mechanical stirrer and a condenser was added polyphosphoric acid (80 gm) and benzene (450 mL). This mixture was heated to reflux for 15 min and then ethyl 4-[(2,2-diethoxy)ethoxy]phenylacetate (86 gm, 0.29 mol) in benzene (50 mL) was added and the reflux was continued for 40 min. The reaction mixture was cooled and the mobile phase was decanted off. This benzene solution was washed successively with H2O, sat. NaHCO3, and sat. NaCl before being dried over Na2SO4, filtered and evaporated to dryness. This residue was dissolved in 10-15% EtOAc in hexane and passed through a short silica gel column (5 cm×10 cm dia.) in the same solvent. The eluent was evaporated to dryness to give a yellow liquid which was further purified by preparative LC using 10% EtOAc in hexane as eluent to give 17.4 gm of ethyl benzofuran-5-ylacetate.

Provenance & Evidence