Reaktion #172293

Reaktionsgleichung

2-hydroxybenzaldehyde

tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate

K2CO3

→

tert-butyl 4-(2-formylphenoxy)piperidine-1-carboxylate

Ausbeute 27.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent DMF was removed by concentration under reduced pressure
2. 2
   workup.ADDITIONThe resulting residue was diluted with EtOAc (100 mL)
3. 3
   Waschenwashed with water (50 mL)
4. 4
   TrocknenThe organic layer was dried (MgSO4)
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by chromatography (pentane/EtOAc=1:10)

Vorschrift

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%).

Quelle