Water → HCID 54545379, compound

Participants

Reaction Steps

Reaction under N2 atmosphere. NaH 60% (0.17 mol) was stirred in tetrahydrofuran (350 ml). A solution of diethyl (cyanomethyl)phosphonate (0.17 mol) in tetrahydrofuran (150 ml) was added dropwise over ±20 minutes. (exothermic temperature rise to 30° C.). The mixture was stirred for 20 minutes at room temperature, then cooled to 0° C. A solution of 5-methyl-3(2H)-benzofuranone (0.15 mol) in tetrahydrofuran (350 ml) was added dropwise over 30 minutes at 0° C. The reaction mixture was stirred overnight at room temperature, then poured out into water (1500 ml) and stirred. This mixture was extracted with ether, diisopropyl ether (2×), dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/hexane 50/50). The desired fractions were collected and the solvent was evaporated, yielding 21.2 g (82%) of 5-methyl-3-benzofuranacetonitrile (interm. 2).

Provenance & Evidence