Ammonium Chloride → HCID 11162207, compound

Participants

Reaction Conditions

Reaction Steps

A dried 50 ml Schlenk tube is charged under an argon atmosphere with a solution of 4.034 mmol of 3-[4-methoxy-3-(3-methoxypropoxy)phenyl]prop-2-yn-1-ol in 20 ml of tetrahydrofuran. The solution is admixed with 0.403 mmol of solid copper(I) iodide and the suspension is cooled to 0° C. Subsequently 6.05 ml of a 2.0 molar isopropyl-magnesium chloride solution in diethyl ether are added. The resulting mixture is stirred at 0° C. over 3.5 hours. The reaction mixture is then poured onto saturated aqueous ammonium chloride solution at 0° C. and then diluted with water and ethyl acetate. The phases are separated; the aqueous phase is extracted with ethyl acetate (2×). The combined organic phases are washed with brine, dried over sodium sulphate, filtered and concentrated by evaporation on a rotary evaporator. The title compound A2 is obtained as a yellow oil (967 mg) from the residue by means of flash chromatography (SiO2 60 F, 2:1 ethyl acetate-hexane). Rf=0.48 (2:1 ethyl acetate-heptane); Rt=3.97 (gradient I).

Provenance & Evidence