Benzyl Chloride → 6-Benzyloxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.98 g (4.73 mMol) 6-hydroxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester [preparation see: J. Am. Chem. Soc. 97 (1974), 7305] in 100 ml acetone, 545 μl (4.73 mMol) benzylchloride, 3.08 g (9.46 mMol) Cs2CO3 und 10 mg NaI are added. Then the mixture is stirred for 2 h at rt and 5 h at 56° C. The reaction mixture is diluted with EtOAc and water, the aq. phase separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated after addition of 10 g SiO2. The resulting powder is put on top of a chromatography column (SiO2) and the title compound eluated with hexan/EtOAc 9:1→8:2→7:3: MS: [M+1]+=298; TLC(hexane/EtOAc 3:1): Rf=0.54.

Provenance & Evidence