Potassium Carbonate → HCID 59472661, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-fluoro-3-cyanobenzaldehyde (3.0 g, 20 mmol) in 20 mL of DMF was treated with 4-methylimidazole (3.0 g, 37 mmol) and warmed to 100° C. Stirred overnight. Diluted with EtOAc, washed with sat'd NaHCO3, dried (Na2SO4), concentrated. Triturated with MeOH and filtered to give a single regioisomer (1.3 g, 6.1 mmol; 31%). Suspended in 20 mL of MeOH, treated with K2CO3 (1.4 g, 10 mmol) and dimethyl (1-diazo-2-oxopropyl)phosphonate (1.4 g, 7.3 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 (606 mg; 15% overall yield):

Provenance & Evidence