1-Benzyl-4-piperidone → 1-Benzylpiperidine-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4.08 g of (methoxymethyl)triphenyl-phosphonium chloride in 20 mL of THF was added 8.11 mL of n-butyllithium(1.6 M in hexane) at 0° C. The reaction was stirred at 0° C. for 0.5 h. To the resulting solution was added 2.05 g of 1-benzyl-4-piperidone at 0° C. After stirring at rt for 1 h, the reaction was refluxed for 3 h. The reaction was cooled to rt and partitioned between EtOAc and H2O. The organic layer was washed with sat'd NaCl, dried over MgSO4 and concentrated to afford 5.48 g of viscous oil. The oil was dissolved in 20 mL of formic acid (96%). After stirring at rt for 4 h, the mixture was concentrated. The residue was dissolved in EtOAc and washed with sat'd NaHCO3 followed by sat'd NaCl. The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 1:1 v/v hexanes/EtOAc followed by EtOAc to give 877 mg of the title compound.

Provenance & Evidence