Imidazole → HCID 59472678, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-fluorobenzaldehyde (5.0 g, 40 mmol) in 60 mL of DMF was treated with 4-methylimidazole (6.6 g, 81 mmol) and K2CO3 (8.4 g, 60 mmol) and warmed to 100° C. Stirred overnight. Diluted with EtOAc, washed with sat'd NaHCO3, dried (Na2SO4), concentrated to give a 4:1 mixture of imidazole regioisomers. Recrystallization from EtOH gave a single regioisomer. A portion of the aldehyde (500 mg, 2.69 mmol) was dissolved in 10 mL of MeOH, treated with K2CO3 (740 mg, 5.4 mmol) and dimethyl (1-diazo-2-oxopropyl)phosphonate (620 mg, 3.2 mmol) and stirred overnight. Diluted with DCM and washed with water. Dried (Na2SO4), conc. Chromatography on silica (0-20% MeOH/DCM) gave the desired alkyne (400 mg; 82%):

Provenance & Evidence