5-Methoxy-1H-inden-1-one → HCID 14742746, compound

Participants

Reaction Steps

A solution of pentyl magnesium bromide (2M; 83 mL) was added with stirring to a chilled (-5° C.) solution of 5-methoxy-1-indenone (24.33 g) in dry tetrahydrofuran (100 mL) and the mixture was stirred at room temperature for 1.5 hours. A few chips of ice were added to destroy excess reagent and after the solvents had been removed under reduced pressure, the residue was taken up in a mixture of dichloromethane (250 mL) and 2N hydrochloric acid and stirred at room temperature for 3 hours. The separated aqueous phase was extracted with dichloromethane (150 mL) then the combined organic layers were dried (MgSO4) and evaporated to provide 30 g of crude product as an oil. Purification of the material by HPLC (dichoromethane-hexane; 2:5) gave 21.62 g of 6-methoxy-3-pentyl-1H-indene as an oil

Provenance & Evidence