Acetic Acid → (S)-3-methyl-4-oxo-4-(2-phenyl-benzoxazol-6-yl)-butyric acid

Participants

Reaction Conditions

Reaction Steps

400 mg (1.46 mmol) 6-bromo-2-phenyl-benzoxazole are dissolved in 15 ml THF and cooled to −70° C., and 1.22 ml (1.92 mmol) n-butyl lithium 1.6M in hexane are added dropwise. This solution chilled to −70° C. is added dropwise to an equally cold −70° C. solution of 220 mg (1.93 mmol) (S)-3-methyl-dihydro-furan-2,5-dione and 15 ml THF. After 15 min stirring the mixture is poured onto semisaturated, acetic acid-containing saline solution and extracted with EA. The org. phase is concentrated by rotary evaporation i. V. and the residue is separated through silica gel (eluant DCM/EA/glacial acetic acid).

Provenance & Evidence