Hydrochloric Acid → Benzofuran-3-acetonitrile

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2.64 grams (0.11 mole) of oil free sodium hydride in 200 milliliters of tetrahydrofuran (THF) was added dropwise a solution of 19.47 grams (0.11 mole) of diethyl cyanomethylphosphonate in 75 milliliters of THF. After the H2 evolution had ceased, a solution of 13.4 grams (0.1 mole) of 3-(2H)-benzo[b]furanone in 100 milliliters of THF was added. The solution was heated at 70° C. for 1.5 hours, cooled, and poured into 500 milliliters of 5% HCl, and worked up using conventional procedures and finally distilled at 96°-100° C./0.075 mm Hg to obtain a yellow oil product which crystallized upon standing.

Provenance & Evidence