Tri(butyl)vinyltin → 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-vinyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

Participants

Reaction Conditions

Reaction Steps

280 mg (0.48 mmol equivalents) of 5-{(4-bromo-2-nitro-1H-imidazol-1-yl)methyl}-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxane was dissolved in 4.7 mL of dimethylformamide, 278 μL (0.95 mmol equivalents) of tributylvinyltin and 55 mg (0.05 mmol equivalents) of tetrakis(triphenylphosphine)palladium were added thereto, and the mixture was heated to 80° C. in an oil bath and then stirred for 5 hours. After completion of the reaction, the reaction liquid was concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1) to give 163 mg (0.30 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-vinyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane.

Provenance & Evidence