Reaktion #172297

Reaktionsgleichung

2-Hydroxybenzaldehyde

2-hydroxybenzaldehyde

N-Boc-3-(methylsulfonyloxy)pyrrolidine

K2CO3

→

tert-butyl 3-(2-formylphenoxy)pyrrolidine-1-carboxylate

Ausbeute 23.7%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeDMF 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
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by chromatography (pentane:EtOAc=1:10)

Vorschrift

2-Hydroxybenzaldehyde (25; 1.2 g, 9.8 mmol), N-Boc-3-(methylsulfonyloxy)pyrrolidine (29; 2.6 g, 9.8 mmol), K2CO3 (2.0 g, 14.7 mmol) and tetrabutyl ammonium iodide (300 mg, cat) in CH2Cl2 (20 mL) was stirred at 70-80° C. for 18 h. DMF was removed by concentration under reduced pressure. The resulting residue was diluted with EtOAc (100 mL), washed with water (50 mL), dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (pentane:EtOAc=1:10) to afford 676 mg of tert-butyl 3-(2-formylphenoxy)pyrrolidine-1-carboxylate 30 as an oil (yield: 23%).

Quelle