Triethylamine → 6-(4-Methoxy-phenylsulfanyl)-hexa-2,4-dienoic acid methyl ester

Temperatur

20 °C

To a solution of 6-bromo-hexa-2,4-dienoic acid methyl ester (1.50 g, 7.3 mmol) and 4-methoxythiophenol (0.93 mL, 7.3 mmol) in tetrahydrofuran (40 mL) was added dropwise triethylamine (1.1 mL, 8.0 mmol) under an atmosphere of argon. The mixture was stirred at 20° C. for one hour, then filtered. The filtrate was concentrated under reduced to pressure and the residue was dissolved in ethyl acetate (50 mL). This solution was washed with saturated aqueous sodium hydrogen carbonate (25 mL), demineralised water (25 mL) and brine (25 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a yellow oil that was purified by column chromatography ((9:1 to 8:2 40-60° C. petroleum ether:diethyl ether) to give the title compound as a colourless oil (1.6 g, 86%).

1. filtrationfiltered
2. concentrationThe filtrate was concentrated
3. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
4. washThis solution was washed with saturated aqueous sodium hydrogen carbonate (25 mL), demineralised water (25 mL) and brine (25 mL)
5. dry with materialThe organic layer was dried over anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto give a yellow oil that
9. customwas purified by column chromatography ((9:1 to 8:2 40-60° C. petroleum ether:diethyl ether)

ORD-Eintrag

ord-2fe57c4e8020410ea5cc5dc79ac2d777

Quelldatensatz

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07683185B2