Water → 4-methoxytetrahydro-2H-pyran-4-carbaldehyde

Participants

Reaction Steps

4-Methoxytetrahydro-2H-pyran-4-carbonitrile (1.00 g, 7.08 mmol) was dissolved in dichloromethane (20 mL). To this, a 1 mol/L solution of diisopropylaluminum hydride in hexane (10.9 mL, 10.9 mmol) was added at −78° C. and the mixture was stirred at room temperature for 30 minutes. The reaction was stopped by addition of water (10.9 mL) at 0° C. The mixture was stirred at room temperature for 1 hour and then filtered through Celite. The solvent was evaporated off under reduced pressure and the residue was dissolved in tetrahydrofuran (10 mL). To this, a 1 mol/L aqueous hydrogen chloride solution was added and the mixture was stirred at room temperature for 30 minutes. The reaction was stopped by addition of a saturated aqueous sodium bicarbonate solution to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to give 4-methoxytetrahydro-2H-pyran-4-carbaldehyde (195 mg, yield: 19%).

Provenance & Evidence