Piperidine → HCID 22481762, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 4-hydroxy-3-iodo-benzoate (9.9 g, 35 mmol) is combined with propioaldehyde diethylacetal (5.6 ml, 39 mmol), bis(triphenylphosphine)palladium(II) chloride (523 mg, 0.7 mmol), cuprous iodide (266 mg, 1.4 mmol), and piperidine (3.9 ml, 39 mmol) in DMF (50 ml) in a dry flask under nitrogen. The reaction is warmed to 60° C. for 6 h and is stirred overnight at RT. The mixture is diluted with EtOAc (250 ml) and is washed with 2:1:1:0.1 water/brine/saturated NaHCO3/conc. NH4OH (4×100 ml). The organic layer is dried (MgSO4) and is concentrated in vacuo to a dark oil. The crude material is chromatographed over 300 g silica gel (230-400 mesh), eluting with 15% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 5.2 g (48%) methyl 2-(diethoxymethyl)-1-benzofuran-5-carboxylate as an amber oil. HRMS (EI) calcd for C15H18O5: 278.1154, found 278.1156 (M)+.

Provenance & Evidence