Imidazole → 6-Triisopropylsilanyloxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester

Participants

Reaction Steps

To a solution of 0.80 g (3.86 mMol) 6-hydroxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester [preparation see: J. Am. Chem. Soc. 97 (1974), 7305] in 8 ml DMF, 1.16 g (17 mMol) imidazol and 2.15 ml chlortriisopropylsilane (95%; 9.7 mMol) are added. After 50 min, the mixture is poured into ice-water and extracted twice with EtOAc. The organic phases are washed with 10% citric acid solution, 2× water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; hexane/EtOAc 29:1) gives the title compound: MS: [M+1]+=364; TLC(hexane/EtOAc 9:1): Rf=0.5.

Provenance & Evidence