Methanol → Methyl 3-(4-(methylthio)phenyl)propanoate

In a 100 mL round bottom flask, 3-(4-(methylthio)phenyl)propanoic acid (1.00 g, 5.10 mmol) was dissolved in DMF (17 mL) under N2(g). CDI (1.24 g, 7.65 mmol) was then added to the reaction mixture and the resulting mixture was allowed to stir at room temperature for ˜45 min. MeOH (6 mL) was then added in dropwise fashion to the reaction. The reaction was allowed to stir for an additional 1 h, after which time it was extracted with EtOAc (3×50 mL) and brine (3×50 mL). The combined organic extracts were dried over anhydrous Na2SO4(s), filtered and concentrated. The crude product was purified by column chromatography (silica gel, gradient elution mixture: 10% EtOAc in Hexanes to 0100% EtOAc) to give the title compound (0.771 g, 72%).

1. stirringto stir for an additional 1 h
2. extractionafter which time it was extracted with EtOAc (3×50 mL) and brine (3×50 mL)
3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4(s)
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude product was purified by column chromatography (silica gel, gradient elution mixture: 10% EtOAc in Hexanes to 0100% EtOAc)

ORD-Eintrag

ord-d092e3bc3c4b40608a671cf9626bb514

Quelldatensatz

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07915443B2