반응 #73718

반응 방정식

ammonium chloride

4

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

n-Butyllithium

→

5

수율 91.0%

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

수율 91.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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%).

출처