Reaktion #2493210

Reaktionsgleichung

Compound 7-1

5-bromo-2-octyloxybenzonitrile

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

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

cesium carbonate

→

[2,2-dimethyl-5-(3-cyano-4-octyloxyphenylethynyl)-1,3-dioxan-5-yl]carbamic acid t-butyl ester

Lösungsmittel

Water

acetonitrile

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 7-1 (0.636 g), (2,2-dimethyl-5-ethynyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester (0.571 g), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.045 g), bis(acetonitrile)palladium(II) dichloride (0.008 g) and cesium carbonate (0.668 g) were stirred in acetonitrile (10 ml) at 70-80° C. for 2 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 [2,2-dimethyl-5-(3-cyano-4-octyloxyphenylethynyl)-1,3-dioxan-5-yl]carbamic acid t-butyl ester as a brown oil. The oil was dissolved in ethyl acetate (6 ml), 10% palladium carbon (about 50% water containing, 0.080 g) was added, and the mixture was stirred at room temperature for 3.5 hr under a hydrogen atmosphere. The solution was filtrated, and the filtrate was concentrated to give the object product (0.610 g) as a pale-yellow powder.

Quelle