Dimethyl Sulfoxide → 1,3-dihydro-1-[2-[5-methoxy-4-[(5-phenylpentyl)oxy]-2-pyridinyl]-2-oxoethyl]-2H-imidazol-2-one

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Reaction Steps

Reaction under N2. A solution of ethanediol dichloride (0.0210 mol) in CH2Cl2 (40 ml) was stirred at −60° C. A solution of dimethyl sulfoxide (0.0420 mol) in CH2Cl2 (10 ml) was added dropwise and stirring was continued for 5 min at −60° C. A solution of 1,3-dihydro-1-[2-hydroxy-2-[5-methoxy-4-[(5-phenylpentyl)oxy]-2-pyridinyl]ethyl]-2H-imidazol-2-one (compound 18) (0.0070 mol) in CH2Cl2 (10 ml) was added dropwise at −60° C. and stirring was continued for 15 min at −60° C. Triethylamine (0.0770 mol) was added dropwise at −60° C. and stirring was continued for 5 min. The mixture was treated with water, then extracted with CH2Cl2. The separated organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 94/6). The pure fractions were collected and the solvent was evaporated, yielding 1.8 g (69.6%) of 1,3-dihydro-1-[2-[5-methoxy-4-[(5-phenylpentyl)oxy]-2-pyridinyl]-2-oxoethyl]-2H-imidazol-2-one (interm. 11).

Provenance & Evidence