18-Crown-6 → 1-Ethenylpyrene

참여 물질

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A 250 mL round-bottomed flask, equipped with a magnetic stirrer, an argon inlet and a Claisen adapter bearing an addition funnel and an argon outlet leading to a mineral oil bubbler, was dried in an oven, assembled hot and cooled under a stream of argon. The flask was charged with methyltriphenyl phosphonium bromide (8.4788 g, 23.73 mmole), potassium t-butoxide (23.7 mL of a 1.0M solution in tetrahydrofuran) and 18-crown-6 (0.180 g). Dry tetrahydrofuran (70 mL) was transferred to the flask under nitrogen using a cannula and the resultant reaction mixture was cooled to 0° C. using an ice-salt bath. Pyrene-1-carboxaldehyde (5.0 g, 21.7 mmole) was dissolved in dry THF (25 mL) and this solution was transferred to the addition funnel, under a nitrogen atmosphere, using a cannula, and then added dropwise to the cold reaction mixture over a period of 10 minutes. The reaction mixture was allowed to warm to room temperature and stirred overnight under an argon atmosphere. The solid which precipitated was filtered, washed with THF (15 mL) on the frit and the combined filtrate was concentrated on a rotary evaporator to give a solid residue, which was dissolved in dry diethyl ether (50 mL). The ether solution was passed through a short bed of neutral alumina washed with ether and the combined ether filtrate was concentrated to give a yellow solid (6.0 g). This yellow solid was chromatographed on silica gel with hexanes as eluent and the chromatographed material thus obtained was further purified by crystallization from 5% water/ethanol to give an off-white crystalline material (2.1655 g), melting point 88°-89° C. (89° C. according to Kamat, P. V.; Basheer, R.; and Fox, M. A. Macromolecules 18, 1366 (1985)).

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