Synthesis
General procedure for the synthesis of tetrahydropyran-4-carbaldehyde from 4-cyanotetrahydropyran: Referring to Example 2. To a solution of toluene (10 mL) containing tetrahydropyran-4-carbonitrile (1.0 g, 9.0 mmol) was slowly added, at -78° C., a solution of diisobutylaluminum hydride (DIBAL-H, 10.8 mL, 10.8 mmol, 1.0 M of the toluene solution ). The reaction mixture was stirred continuously at -78 °C for 1 h, followed by slow warming to room temperature. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product tetrahydropyran-4-carbaldehyde (530 mg, 52% yield).
