Hexanoic Acid → (5R)-3-(4-hexanoyloxyphenyl)-5-phenyl-2-oxazolidinone

Participants

Reaction Steps

0.50 g (1.96 mM) of (5R)-3-(4-hydroxyphenyl)-5-phenyl-2-oxazolidinone synthesized in Example 2, 0.26 g of hexanoic acid and 20 ml of methylene chloride were placed in 50 ml-round bottomed flask, followed by stirring to form a solution. To the solution, 0.43 g (2.08 mM) of N,N'-dicyclohexylcarbodiimide and 0.10 g of 4-dimethylaminopyridine were added in succession, followed by stirring for 8 hours at room temperature. The precipitated N,N'-dicyclohexylurea was filtered out and the filtrate was evaporated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=20/1) and recrystallized from methanol to obtain 0.36 g of (5R)-3-(4-hexanoyloxyphenyl)-5-phenyl-2-oxazolidinone (Yield: 52.0%).

Provenance & Evidence