2-(Trimethylsilyl)ethanethiol → 2-Cyano-4-(3-furyl)-7-mercaptonaphthalene

Participants

Reaction Steps

A mixture of 2-cyano-4-(3-furyl)-7-iodonaphthalene (1 g), 2-(trimethylsilyl)ethane thiol (390 mg), potassium tert-butoxide (650 mg) and tetrakis (triphenylphosphine)palladium (100 mg) in EtOH (5 mL) was reluxed for 90 min. The solvent was evaporated and the residue partitioned between Et2O and H2O. The organic phase was dried (MgSO4) and concentrated and the residue was dissolved in DMF (24 mL). To this solution was added Bu4NF (7.7 mL of a 1M THF solution). After 30 min., 1N HCl was added followed by H2O. The precipitate that formed was filtered and washed with H2O to provide the title compound as a solid.

Provenance & Evidence