4-{[(1-Phenyl-1H-pyrazol-3-yl)oxy]methyl}-1,3-dioxolan-2-one

Abstract

Abstract:The title compound was obtained by the reaction of tosylated glycerol carbonate with 1-phenyl-1H-pyrazol-3-ol in a good 71% yield. Detailed spectroscopic data ( 1 H-NMR, 13 C-NMR, 15 N-NMR, IR, MS) are presented.Keywords: 1H-pyrazol-3-ol; glycerol; tosylated glycerol 1,2-carbonate; alkylation 1-Phenylpyrazole derivatives are known to have a broad spectrum of biological activities [1][2][3][4][5][6]. Recently, 1-phenyl-1H-pyrazol-3-ol was used as a versatile synthon for the preparation of various (het)aryl-and carbo-functionally substituted pyrazole derivatives employing Pd-catalyzed crosscoupling reactions [7,8]. In the present work, functionalization of 1-phenyl-1H-pyrazol-3-ol with tosylated glycerol 1,2-carbonate (TGC) was investigated. TGC is relatively new and efficient reagent, which have found application as an initiator of cationic ring-opening polymerization [9] and as a versatile bis-electrophile to access new functionalized glycidol derivatives [10,11]. TGC can be easily obtained by tosylation of glycerol carbonate (4-(hydroxymethyl)-1,3-dioxan-2-one) [10], the latter is an industrial product of glycerol valorization [12].It is known that TGC reacts with 4-methoxyphenol in DMF in the presence of K 2 CO 3 to afford Oalkylated product, 4-(3-methoxyphenoxy)methyl-1,3-dioxolan-2-one, in only 41% yield [11], while 55% of the arylsulfanyl analogue is obtained in analogous conditions from m-methoxythiophenol [10]. The reaction of 1-phenyl-1H-pyrazol-3-ol 1 with TGC 2 was carried out in DMF in the presence of K 2 CO 3 and gave chemoselectively 4-{[(1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-1,3-dioxolan-2-one 3 in 71% isolated yield. The structure of compound 3 was confirmed by its spectroscopic data ( 1 H NMR, 13 C and 15 N NMR, IR, MS) as well as by elemental analysis. OPEN ACCESS