Sodium t-butoxide → 1-(3-Methoxypropyl)-3,3,6-trimethyl-1,3-dihydroindol-2-one

Participants

Reaction Conditions

Reaction Steps

The solution, prepared under argon, of 0.226 g of 1,3-bis(2,6-Di-L-propylphenyl)imidazolium chloride, 0.116 g of palladium(II) acetate and 1.497 g of sodium tert-butoxide in 90 ml of dioxane is admixed with stirring with the solution of 3.34 g of N-(2-bromo-5-methylphenyl)-N-(3-methoxypropyl)isobutyramide in 10 ml of dioxane and stirred at 50° C. over 22 hours. The reaction mixture is cooled, poured onto ice-water (250 ml) and extracted with tert-butyl methyl ether (2×250 ml). The organic phases are washed successively with water (2×250 ml) and brine (1×250 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.26 (1:1 EtOAc-heptane); Rt=16.60 (II).

Provenance & Evidence