Reaktion #172449

Reaktionsgleichung

water

8-methoxy-9-[2-(thiophene-2-yl)vinyl]-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine

n-butyllithium

water

N,N-dimethylformamide

→

5-[2-(8-methoxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-9-yl)vinyl]thiophene-2-carboaldehyde

Ausbeute 35.5%

Lösungsmittel

tetrahydrofuran

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGThe reaction mixture was stirred for 1 hour
3. 3
   Waschenwashing with a saturated saline solution
4. 4
   Trocknendrying over anhydrous sodium sulfate, and concentration
5. 5
   workup.DISSOLUTIONThe residual liquid was dissolved in 300 ml of ether
6. 6
   workup.ADDITION50 mg of iodine pieces were added
7. 7
   workup.STIRRINGAfter stirred at room temperature
8. 8
   Waschenthe mixture was washed with a 5% sodium bisulfite solution
9. 9
   TrocknenDrying over anhydrous sodium sulfate and concentration
10. 10
    SonstigeThe residue was purified by silica gel column chromatography
11. 11
    Sonstigeto give 496 mg of a dark reddish brown oily matter (yield: 35.5%)

Vorschrift

In a stream of argon, in 25 ml of tetrahydrofuran was dissolved 1.29 g (4.14 mmol) of 8-methoxy-9-[2-(thiophene-2-yl)vinyl]-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine, and 3.9 ml of n-butyllithium (1.6 mol solution in hexane) (6.24 mmol) was added dropwise thereto under cooling at −70° C. After the mixture was stirred for 1 hour, 0.43 g (5.88 mmol) of N,N-dimethylformamide was added dropwise thereto. The reaction mixture was stirred for 1 hour and the temperature was allowed to rise. To this mixture, 10 ml of water was added dropwise. After the reaction mixture was added to water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residual liquid was dissolved in 300 ml of ether and 50 mg of iodine pieces were added thereto. After stirred at room temperature, the mixture was washed with a 5% sodium bisulfite solution and then with a saturated saline solution. Drying over anhydrous sodium sulfate and concentration were performed. The residue was purified by silica gel column chromatography to give 496 mg of a dark reddish brown oily matter (yield: 35.5%).

Quelle