Benzaldehyde → HCID 54699181, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of lithium diisopropylamide (1.1 m mol) in tetrahydrofuran (16 ml) was added N-methyl-3-(3-dodecyloxyphenyl)-4-hydroxy-3-pyrrolin-2-one (0.19 g, 0.5 m mol) at -78° C. and the mixture was stirred for 5 minutes at 0° C. The reaction mixture was cooled to -78° C. and, to this, was added benzaldehyde (0.15 ml, 1.5 m mol), stirring for 30 minutes. A saturated aqueous ammonium chloride solution (20 ml) was added to the reaction mixture and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=1:1) to obtain two diastereomers of N-methyl-3-(3-dodecyloxyphenyl)-4-hydroxy-5-hydroxy-(phenyl)methyl-3-pyrrolin-2-one [diastereomer A (5-j): 0.10 g, diastereomer B (5-k): 0.05 g]. The former was recrystallized from IPE to give crystals of m.p. 117°-118° C. and the latter was recrysrtallized from methanol to give crystals of m.p. 110°-111° C.

Provenance & Evidence