1-Iodooctane → (5R)-3-(4-octyloxyphenyl)-5-phenyl-2-oxazolidinone

Participants

Reaction Steps

Then, 0.30 g (1.18 mM) of (5R)-3-(4-hydroxyphenyl)-5-phenyl-2-oxazolidinone and 4.6 ml of DMF were placed in 30 ml-round bottomed flask, followed by stirring to form a solution. To the solution, 0.053 g (1.33 mM) of 60%-oily sodium hydride was added under stirring at room temperature. After the settlement of foaming, 0.25 ml (1.38 mM) of 1-iodooctane was added to the mixture, followed by stirring for 30 minutes on an oil bath kept at about 70° C. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by purification by silica gel column chromatography (eluent: toluene/ethyl acetate =100/1) and recrystallization from a toluene-methanol mixture solvent to obtain 0.13 g of (5R)-3-(4-octyloxyphenyl)-5-phenyl-2-oxazolidinone (Yield: 30.1%).

Provenance & Evidence