Toluene → HCID 22714048, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 598 (0.05 g, 0.011 mmol) in toluene (2 ml) under N2 was added thionyl chloride (1 ml) and heated at reflux for 3 h. The solution was concentrated using toluene to azeotrope. To a solution of diethylzinc (1 ml, 1 mmol) under N2 stirring at −20° C. was added a solution of CuCN (0.093 g, 1.04 mmol) and LiCl (0.086 g, 2.02 mmol) in THF (1.5 ml). This mixture was gradually allowed to warm to 0° C., stirred for 15 min at this temperature, and cooled to −25° C. To this solution was added the acid chloride residue in THF (0.5 ml) and stirred for 1.5 h gradually allowing to warm to 0° C. The reaction was diluted with NH4Cl(aq) and extracted with dichloromethane (2×). The combined organic layers were washed (brine), dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, acetone/dichloromethane gradient) gave the title compound (0.013 g, 28%).

Provenance & Evidence