Water → HCID 13055759, compound

Participants

Reaction Steps

2.78 g (15 mmol) of p-bromo-ethylbenzene were added dropwise to a stirred suspension of 0.36 g (15 mg-atoms) of magnesium turnings in 25 ml of anhydrous tetrahydrofuran containing an iodine crystal to form a Grignard reagent and the resulting solution was added dropwise to a suspension of 2.26 g (10 mmol) of the product of Step B in 50 ml of anhydrous tetrahydrofuran. The mixture was stirred at room temperature for one hour and was poured into 200 ml of water. The mixture was extracted with 200 ml of chloroform and was filtered through a celite pad. The separated aqueous phase was extracted twice with 100 ml of chloroform and the combined organic phases were dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure to obtain a green gum. The latter was chromatographed over 200 g of silica gel and was eluted with a 95-5 chloroform-methanol mixture to obtain 2.12 g (64% yield) of (4-ethyl-phenyl)(5-methoxy-imidazo[1,2-a] quinolin-2-yl)-methanol in the form of a green gum.

Provenance & Evidence