5-methylsulfanylfuran-2-carbaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-(methylthio)furan-2-carbaldehyde (1.0 g, 7.04 mmol) in ethanol (10 mL) was added an aqueous solution of hydroxylamine hydrochloride (3.75M) (2.26 mL, 8.45 mmol) and an aqueous solution of sodium acetate (1.5 M) (3.78 mL, 5.63 mmol). The reaction mixture was stirred a 23° C. for 18 hours. The ethanol was concentrated in vacuo, H2O was added (50 mL) and the precipitate was filtered and dried in oven (60° C.) for 10 minutes to afford 277 mg (25%) of the title compound. LCMS (+ESI, M+H+) m/z 158. The ethanol was concentrated in vacuo, H2O was added (50 mL) the precipitate was filtered dried in oven (60° C.) for 10 minutes

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The reaction mixture was stirred at −78° C. for 30 min by warming to 0° C. for 1 hour the organic material was extracted with ether (2×50 mL) The combined organic fractions were dried (MgSO4) concentrated in vacuo