Benzenepropanal → HCID 53809102, compound

Participants

Reaction Steps

A mixture of 5.90 g of L-leucine benzyl ester p-toluenesulfonate, 2.01 g of 3-phenylpropionaldehyde and 2.09 ml of triethylamine in 100 ml of toluene was heated to reflux in a Dean-Stark apparatus for 2 hours. The mixture was allowed to cool, and then 1.93 ml of diethyl phosphite was added to the mixture. Then the mixture was heated to reflux for 27 hours, and then allowed to cool. The mixture was successively washed with 100 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (chloroform: ethyl acetate=10: 1, and hexane: ethyl acetate=1: 1) to yield the title compound as a mixture of stereoisomers, a light-yellow oil (1.87 g).

Provenance & Evidence