Tetrahydrofuran → HCID 58174493, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-tolylsulfanyl)-phenyl bromide (6.98 g, 25 mmol) was dissolved in heptanes (40 mL) and dry tetrahydrofuran (4.1 mL) and after 1.5 hrs the reaction mixture was cooled down to 0° C. under an atmosphere of nitrogen. n-Butyl lithium in heptanes 2.7 M (9.8 mL, 26.5 mmol) was added at 0° C. and after 45 minutes the reaction mixture was cooled to −15° C. A solution of N-benzyloxy-4-piperidone (5.08 g, 25 mmol) in dry tetrahydrofuran (40 mL) was added to the reaction mixture maintaining the temperature below −15° C. Once the addition was complete the reaction was allowed to warm to room temperature before quenching with dilute aqueous HCl solution. HPLC indicated the presence of 1-methyl-4-phenylsulfanyl-benzene and a complex mixture of unknown compounds.

Provenance & Evidence