Pyridine → 1-(3,5-Bis(methoxycarbonyl)phenyl)-2-(1-adamantyl)ethyne

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Reaction Steps

In a 1 L four-neck flask provided with a thermometer, a Dimroth condenser, a nitrogen inlet pipe and an agitator, 125 g of dimethyl 5-bromoisophthalate (0.458 mol), 1.1 g of triphenyl phosphine (0.00419 mol), 0.275 g of copper iodide (0.00144 mol) and 64.26 g of the obtained 1-ethynyladamantane (0.401 mol) were charged and nitrogen was passed into the flask. Then, 375 mL of dehydrated triethylamine and 200 mL of dehydrated pyridine were added therein and the mixture was agitated and dissolved. After nitrogen was passed into the flask for one hour, 0.3 g of dichlorobis (triphenyl phosphine) palladium (0.000427 mol) was quickly added and the mixture was heated and refluxed in an oil bath. Then, triethylamine and pyridine was removed under reduced pressure to obtain a brown viscous solution. The solution was added to 500 mL of water and filtered to separate a solid. The solid was washed with 500 mL of water, 500 mL of 5 mol/L hydrochloric acid and 500 mL of water each two times and dried under pressure at 50° C., thus obtaining 121.5 g of 1-(3,5-bis(methoxycarbonyl)phenyl)-2-(1-adamantyl)ethyne (the yield was 86%).

Provenance & Evidence