3-Furancarboxaldehyde, tetrahydro- → HCID 72305307, compound

Participants

Reaction Steps

Tetrahydrofuran-3-carboxaldehyde (50% solution in water, 2.5 mL, 12.5 mmol) in ethanol (5.0 mL) is stirred with hydroxylamine-hydrochloride (1.3 g, 18.7 mmol) for 3 h. The reaction is quenched with 0.1 M HCl and extracted with EtOAc, dried over MgSO4, filtered, and concentrated to give the oxime as a colorless oil. A solution of the oxime (115 mg, 1.0 mmol) in DMF (1 mL) is then treated with N-chlorosuccinimide (147 mg, 1.1 mmol) at 40° C. for 2 h. The reaction is then cooled to room temperature, poured on to ice water and extracted with diethyl ether (3×10 mL). The combined organics are dried over MgSO4, filtered, and concentrated to give tetrahydrofuran-3-carbonyl chloride oxime, which is used without further purification.

Provenance & Evidence