Water → HCID 86657939, compound

Participants

Reaction Steps

4-(Trimethylsilyloxy)tetrahydro-2H-pyran-4-carbonitrile (1.00 g, 5.02 mmol) was dissolved in dichloromethane (20 mL). To this, a 1 mol/L solution of diisopropylaluminum hydride in hexane (7.76 mL, 7.76 mmol) was added at −78° C. and the mixture was stirred at room temperature for 20 minutes. The reaction was stopped by addition of water (7.76 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 saturated aqueous ammonium chloride solution was added and the mixture was stirred at room temperature for 30 minutes. Then, 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-(trimethylsilyloxy)tetrahydro-2H-pyran-4-carbaldehyde (297 mg, yield: 29%).

Provenance & Evidence