Dimethylformamide → HCID 90285208, compound

Participants

Reaction Conditions

Reaction Steps

A flame-dried 50 mL Schlenk flask was equipped with sodium methanolate (1.90 g, 35.1 mmol, 6.5 mL; 5.4 M in MeOH), copper(I) iodide (0.77 g, 4.05 mmol) and 2,6-dibromo-4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine (0.21 g, 0.40 mmol), suspended in N,N-dimethylformamide (12.4 mL) and degassed with argon for 30 min. This mixture was stirred under an atmosphere of argon at 100° C. overnight. The reaction was stopped by addition of aqueous NH4Cl solution and the resulting mixture was extracted with CH2Cl2 (3×). The combined organic fractions were dried with MgSO4, filtered and the solvents were evaporated. The crude product was purified by column chromatography (silica, n-hexane/EtOAc 8:1) yielding 2,6-dimethoxy-4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine as a greenish oil (0.12 g, 70%).

Provenance & Evidence