Tetrabutylammonium Fluoride → 2,2-dimethyl-5-hydroxymethyl-5-[(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

Participants

Reaction Conditions

Reaction Steps

86 mg (0.15 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane was dissolved in 1.0 mL of tetrahydrofuran, 0.17 mL (1 mol/L solution, 0.17 mmol equivalents) of a solution of tetrabutylammonium fluoride in tetrahydrofuran was added thereto, and the mixture was stirred at room temperature (25° C.) for 10 minutes. After completion of the reaction, the solvent was removed by distillation, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/1) to give 47 mg (0.14 mmol equivalents) of 2,2-dimethyl-5-hydroxymethyl-5-{(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl}-1,3-dioxane.

Provenance & Evidence