N,N-Diethylethanamine trihydrofluoride → 8-Hydroxyquinoline

Participants

Reaction Steps

To a 300 mL flask was added 6.7 g of 5-(4-t-butyl-phenyl)-2-methyl-8-t-butyldimethylsiloxyquinoline and 100 ml dry THF. The mixture was stirred under nitrogen while 13.5 ml triethylamine trihydrofluoride (Aldrich) was added in 5 portions over 30 min. The reaction mixture was stirred at room temperature for 2 h and the solvents removed in vacuo. The resulting oil was purified by silica chromatography, first eluting with 15% dichloromethane in hexanes and then collecting the product by elution with 50% dichloromethane in hexanes to give 4.33 g of the desired product quinaldine 2a as a colorless solid.

Provenance & Evidence