Hydrochloric Acid → 2-Furancarboxaldehyde, 5-(methylthio)-

Temperatur

-78 °C

To a solution of 2-(diethoxymethyl)furan (2.00 g, 11.75 mmol) in dry THF (8 mL) was added a solution of n-BuLi (1.6 M in Hexane) (8.80 mL, 14.1 mmol) at −78° C. The resulting mixture was stirred at −78° C. for 1 h and treated with methyldisulfide (1.06 mL, 11.75 mmol). The reaction mixture was stirred at −78° C. for 30 min followed by warming to 0° C. for 1 hour. HCl (1N) (20 mL) was added and the organic material was extracted with ether (2×50 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to afford 1.58 g (94%) of crude title compound. LCMS (+ESI, M+H+) m/z 143.

1. stirringThe reaction mixture was stirred at −78° C. for 30 min
2. temperatureby warming to 0° C. for 1 hour
3. extractionthe organic material was extracted with ether (2×50 mL)
4. dry with materialThe combined organic fractions were dried (MgSO4)
5. concentrationconcentrated in vacuo

ORD-Eintrag

ord-724ef3e92dc34a918f6904ee3cec4102

Quelldatensatz

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07893055B2