Reaktion #1180489

Reaktionsgleichung

cesium carbonate

Compound 1-1

5-bromo-2-(3-phenylpropoxy)benzonitrile

(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester

2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

→

(5-{2-[3-cyano-4-(3-phenylpropoxy)phenyl]ethynyl}-2,2-dimethyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester

Lösungsmittel

acetonitrile

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate
2. 2
   Waschenwashed with saturated brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

Compound 1-1 (0.720 g), (5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester (0.634 g) synthesized according to the known method (e.g., Tetrahedron vol.57 (2001) pages 6531-6538), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.050 g), bis(acetonitrile)palladium(II) dichloride (0.009 g) and cesium carbonate (0.855 g) were stirred in acetonitrile (8.7 ml) at 70° C. for 7 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give (5-{2-[3-cyano-4-(3-phenylpropoxy)phenyl]ethynyl}-2,2-dimethyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester as a pale-brown solid. This solid was dissolved in ethyl acetate (5 ml), 10% palladium carbon (containing water about 50%, 0.044 g) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hr. The solution was filtered, and the filtrate was concentrated to give the object product (0.408 g) as a brown oil.

Quelle