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

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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.

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