[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH:13]1[CH2:15][CH:14]1[C:16]([O:18]CC)=[O:17].O.[OH-].[Li+].CO.Cl>O1CCCC1.O.C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH:13]1[CH2:15][CH:14]1[C:16]([OH:18])=[O:17]
To a solution of ethyl 2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylate (746 mg, 2.76 mmol) in tetrahydrofuran (15 mL) was added lithium hydroxide monohydrate (232 mg, 5.52 mmol) in water (5.00 mL) at rt. Added methanol (5.00 mL) and stirred for 15 h at rt. Removed solvent. Obtained a white solid. Redissolved in water (15 mL) and neutralized with 5.5 mL of 1.0 M HCl. Removed solvent and azetroped with toluene (2×10 mL). Dried for 20 h and obtained 2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylic acid as a white powder. MS (ESI) 243 (M+H); Rf=1.35 (Condition A).
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