Hydrochloric Acid → HCID 86702314, compound

Participants

Reaction Conditions

Reaction Steps

6,8-Dibromo-3-(4-methoxy-phenyl)-chromen-2-one (30.8 g, 75.1 mmol), copper(1)iodide (1.50 g, 7.88 mmol) and bis(acetonitril)palladium(II) chloride (5.00 g, 7.12 mmol) are dissolved in 300 ml DMF and 50 ml diisopropylamin at 70° C., and a solution of butyne-1-ol (20.0 g, 285 mmol) in 50 ml DMF is added dropwise within 30 min. The reaction mixture is stirred overnight at 80° C., then poured onto 300 ml water and acidified with 2 N hydrochloric acid. The precipitated product is filtered by vacuum, then filtered through silica gel with THF/toluene (4:1) and addition of a small amount of ethanol, and the crude product is recrystallized from toluene. 6,8-Bis-(4-hydroxy-but-1-ynyl)-3-(4-methoxy-phenyl)-chromen-2-one is obtained as light brown solid, which is pure enough to be used as starting material for the next step.

Provenance & Evidence