Reaktion #47630

Reaktionsgleichung

oxalyl chloride

bicyclo[2.2.1]hept-2-yl-methanol

triethylamine

dimethyl sulfoxide

→

bicyclo[2.2.1]heptane-2-carbaldehyde

Ausbeute 103.1%

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a flask under argon was placed
2. 2
   workup.STIRRINGThe mixture was stirred at −78° C. for another 15 min
3. 3
   Temperaturthe reaction was slowly warmed to 0° C
4. 4
   SonstigeThe mixture was then quenched with a 1M aqueous sodium bisulfate solution (50 mL)
5. 5
   Extraktionextracted with dichloromethane (3×20 mL)
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigePurification by AnaLogix IntelliFlash flash chromatography (12 g column, 3% ethyl acetate/hexanes to 40% ethyl acetate/hexanes)

Vorschrift

In a flask under argon was placed dichloromethane (25 mL) and to this was added a 2M solution of oxalyl chloride in dichloromethane (4.0 mL, 8.0 mmol). The mixture was then cooled to −78° C. and then slowly treated with dimethyl sulfoxide (846 μL, 11.92 mmol) and gas evolution occurred. The mixture was stirred at −78° C. for 20 min. After this time, a solution of bicyclo[2.2.1]hept-2-yl-methanol (505 mg, 4.0 mmol) in dichloromethane (15 mL) was added dropwise. The mixture was stirred at −78° C. for another 15 min and then triethylamine (2.2 mL, 15.6 mmol) was added and the reaction was slowly warmed to 0° C. The mixture was then quenched with a 1M aqueous sodium bisulfate solution (50 mL) and extracted with dichloromethane (3×20 mL). The organic layers were combined and dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by AnaLogix IntelliFlash flash chromatography (12 g column, 3% ethyl acetate/hexanes to 40% ethyl acetate/hexanes) afforded slightly impure bicyclo[2.2.1]heptane-2-carbaldehyde (512 mg).

Quelle