Reaktion #73718

Reaktionsgleichung

ammonium chloride

4

(2-(Benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanone

n-Butyllithium

→

5

Ausbeute 91.0%

2-(3-(1-(2-(Benzyloxy)-3-tert-butylphenyl)vinyl)phenyl)pyridine

Ausbeute 91.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedid not exceed 3° C
2. 2
   workup.STIRRINGStirring
3. 3
   TemperaturThe reaction mixture was cooled on an ice bath
4. 4
   Sonstigedid not exceed 3° C
5. 5
   workup.STIRRINGStirring
6. 6
   workup.WAITwas continued at room temperature overnight
7. 7
   Extraktionextracted with ethyl acetate (150 mL)
8. 8
   ExtraktionThe organic extract
9. 9
   Waschenwas washed with water (2×80 mL)
10. 10
    Trocknendried over sodium sulfate
11. 11
    SonstigeThe solvent was removed on a rotary evaporator
12. 12
    Sonstigethe crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (2 L)

Vorschrift

Methyl triphenylphosphonium bromide (2.2 g, 6.17 mmol) was suspended in anhydrous tetrahydrofuran (20 mL) and stirred under nitrogen on an ice bath. 2.5M n-Butyllithium in hexanes (2.3 mL, 5.75 mmol) was added at such a rate that temperature did not exceed 3° C. Stirring was continued at room temperature for 1 hr. The reaction mixture was cooled on an ice bath and a solution of 4 (1.3 g, 3.08 mmol) in tetrahydrofuran (8 mL) was added at such a rate that temperature did not exceed 3° C. Stirring was continued at room temperature overnight. The reaction mixture was poured on saturated ammonium chloride (150 mL) and extracted with ethyl acetate (150 mL). The organic extract was washed with water (2×80 mL) and dried over sodium sulfate. The solvent was removed on a rotary evaporator and the crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (2 L), then 4% (4 L) to produce 5 (1.18 g, 91%).

Quelle