Reaktion #619427

Reaktionsgleichung

N-methoxy-N-methylpropionamide

lithium diisopropylamide

2-iodothiophene

→

title compound

Ausbeute 49.0%

1-(5-iodothiophen-2-yl)propan-1-one

Ausbeute 49.0%

Lösungsmittel

THF

THF

THF heptane ethylbenzene

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a nitrogen inlet
2. 2
   workup.ADDITIONwas added with vigorous stirring
3. 3
   TemperaturAfter 10 minutes the mixture was warmed to −10° C.
4. 4
   TemperaturThe reaction mixture was re-cooled to −40° C.
5. 5
   workup.ADDITIONwas added in one portion
6. 6
   Temperaturto warm slowly to 0° C.
7. 7
   Sonstigethe reaction was quenched with saturated 50 ml of NH4Cl solution
8. 8
   ExtraktionThe contents were extracted with 3×100 ml of DCM
9. 9
   Trocknendried over MgSO4
10. 10
    Einengenconcentrated
11. 11
    Sonstigeto give an oily residue
12. 12
    SonstigeThis was purified by flash chromatography

Vorschrift

38.4 ml of a 2M solution of lithium diisopropylamide (8.2 g, 76.8 mmol) in THF-heptane-ethylbenzene was added to THF (50 ml) taken in a 500 three neck RB flask equipped with a nitrogen inlet. The mixture was cooled to −40° C. and then 2-iodothiophene (16.1 g, 76.8 mmol) taken in 50 ml of THF was added with vigorous stirring. After 10 minutes the mixture was warmed to −10° C. and stirred for 30 min. The reaction mixture was re-cooled to −40° C. and N-methoxy-N-methylpropionamide (9 g, 76.8 mmol) taken in 50 ml of THF was added in one portion. The reaction mixture was allowed to warm slowly to 0° C. and then the reaction was quenched with saturated 50 ml of NH4Cl solution. The contents were extracted with 3×100 ml of DCM, dried over MgSO4 and concentrated to give an oily residue. This was purified by flash chromatography to give the title compound (10 g, 49%).

Quelle