Synthesis of 2, 4 (5)-bis (hydroxymethyl) imidazoles and 2, 4 (5)-bis [(2-hydroxyethoxy) methyl] imidazoles. Precursors of 2, 4 (5)-connected imidazole crown ethers

SC Zimmerman, KD Cramer…

Index: Zimmerman, Steven C.; Cramer, Katherine D.; Galan, Adam A. Journal of Organic Chemistry, 1989 , vol. 54, # 6 p. 1256 - 1264

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Citation Number: 18

Abstract

Two syntheses of l-[(dimethylamino) sulfonyl]-2, 4-bis [(2-hydroxyethoxy) methyl] imidazole, 3, a precursor to imidazole-containing crown ethers, are described. The first involved hydroxymethylation of 1-benzylimidazole with formaldehyde to afford l-benzyl-2, 5-bis (hydroxymethyl) imidazole(5)(20% yield), which was elaborated into 3 in four steps. An alternative and more efficient route involved coupling of diamine 17b with the imino ether ...