Synthesis
The general procedure for the synthesis of (R)-3-iodotetrahydrofuran from (S)-3-iodotetrahydrofuran was as follows: to a solution of (S)-tetrahydrofuran-3-ol (983 mg, 11.16 mmol) in dichloromethane (50 mL) was added triphenylphosphine (5.0 g, 21.20 mmol), glyoxal (1.4 g, 21.20 mmol) and iodine (5.0 g, 21.20 mmol). The reaction mixture was refluxed overnight, cooled and the reaction was quenched with saturated sodium thiosulfate solution. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a yellow solid. The solid was ground with hexane at room temperature for 2 h. The filtrate was concentrated after filtration. Finally, it was purified by silica gel column chromatography with ethyl acetate/hexane (0-5%) as eluent for 20 min to give (R)-3-iodotetrahydrofuran as a clear oil (1.0 g, 52% yield).
