Salicylaldehyde → Tert-butyl 4-(2-formylphenoxy)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture containing 2-hydroxybenzaldehyde (25; 4.2 g, 34.5 mmol), tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (24; 15.0 g, ˜41 mmol), K2CO3 (7.15 g, 51.7 mmol) and tetrabutyl ammonium iodide (500 mg, cat) in DMF (100 mL) was stirred at 70-80° C. for 18 h. The solvent DMF was removed by concentration under reduced pressure. The resulting residue was diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (pentane/EtOAc=1:10) to give tert-butyl 4-(2-formylphenoxy)piperidine-1-carboxylate 26 as a yellow oil (2.89 g, 27%).

Provenance & Evidence