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nommée couplage de Glaser, qui est favorisée par la présence d'oxygène. 133,134,135 Le mécanisme proposé est radicalaire (Schéma 32) 136 Le 4-éthynylanisole 71 réagirait de façon classique avec l'iodure de cuivre (I) pour donner l'alcyne cuivreux. Ce dernier, en présence d'oxygène dans le milieu, serait oxydé en alcyne cuivrique, Puis, une rupture homolytique de la liaison carbone-cuivre (II) aurait lieu générant le radical alcyne. Celui-ci réagirait avec un autre radical alcyne conduisant à la formation du dimère 76 ,
alcyne réagiraient ensemble dans une réaction de couplage de Sonogashira en présence de palladium (0) provenant de PdCl 2 (PPh 3 ) 2 et de cuivre (I) pour former le phénol éthylynique. Le cuivre (I) prendrait immédiatement le relais en se complexant à la triple liaison de l'alcyne et en présence d'une base ,
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mmol, 9 éq, p.31 ,
celui-ci est filtré sur Célite ® et est lavé avec de l'éthanol ainsi qu'avec de l'acétate d'éthyle. Le filtrat jaune est concentré sous pression réduite. Le résidu obtenu est ensuite solubilisé dans une solution d'acide chlorhydrique 1N et de l'acétate d'éthyle. Le mélange est extrait deux fois avec de l'acétate d'éthyle. Les phases organiques rassemblées sont séchées sur MgSO 4 puis concentrées sous pression réduite. Le produit brut obtenu est purifié par chromatographie sur colonne de silice prépackée (éluant : gradient heptane à AcOEt, p.4 ,
050 g, 0,20 mmol, 1 éq ,
éthyle et une solution d'acide chlorhydrique 1N sont ajoutés au milieu qui est extrait deux fois avec de l'acétate d'éthyle. Les phases organiques rassemblées sont lavées une fois avec une solution d'acide chlorhydrique 1N, une fois avec une solution aqueuse saturée en NaCl, séchées sur MgSO 4 et concentrées sous pression réduite. Le produit brut obtenu est purifié par chromatographie sur colonne de silice prépackée (éluant : gradient heptane à heptane, AcOEt, vol.8, issue.2 ,
050 g, 69 %) sous la forme d'un solide amorphe blanc ,
100 g, 0,17 mmol) est solubilisée dans une solution d'acide chlorhydrique à 10 % dans le méthanol (3 ml) Le mélange réactionnel est agité à reflux pendant 2 ,
Le précipité formé est filtré sur Büchner, est lavé avec de l'eau et est séché afin d'obtenir la flavone 230 (0,092 g, rendement quantitatif) ,
077 g, 0,20 mmol, 1 éq.), de l'alcyne bromé 234, p.59 ,
026 g, 22 %) sous la forme d'un solide amorphe jaune ,
acidifié avec une solution d'acide chlorhydrique 1N et est extrait deux fois avec de l'acétate d'éthyle. Les phases organiques rassemblées sont lavées quatre fois avec une solution aqueuse saturée en NaCl, séchées sur MgSO 4 et concentrées sous pression réduite. Le produit brut obtenu est purifié par chromatographie sur colonne de silice prépackée (éluant : gradient toluène à toluène, AcOEt, vol.8, issue.2 ,
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