Reaktion #1540813

Reaktionsgleichung

1-iodoheptane

Sodium hydride

6-acetyl-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one

Compound 28

6-acetyl-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one

→

title compound

Ausbeute 66.0%

N-Heptyl-6-acetyl-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one

Ausbeute 66.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe ice-bath was removed
2. 2
   workup.STIRRINGto stir for 2 h
3. 3
   Sonstigequenched with ice water
4. 4
   ExtraktionThe resulting solution was then extracted with ether (3×10 mL)
5. 5
   Waschenwashed with brine (1×10 mL)
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated at reduced pressure
8. 8
   SonstigePurification by flash chromatography (75:25 hexane/ethyl acetate)

Vorschrift

Sodium hydride (21.0 mg, 90.0 mmol) was slowly added into a solution of 6-acetyl-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (Compound 28, 98.0 mg, 45.0 mmol) in 3 mL of DMF at 0° C. After stirring at 0° C. for 10 min, 1-iodoheptane (30.5 mg, 135.0 mmol) was added to the reaction mixture and the ice-bath was removed. The reaction mixture was allowed to stir for 2 h and then quenched with ice water. The resulting solution was then extracted with ether (3×10 mL), washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (75:25 hexane/ethyl acetate) yielded the title compound (93.6 mg, 66% yield) as a colorless oil:

Quelle