Water → HCID 86657939, compound

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%).

1. stirringThe mixture was stirred at room temperature for 1 hour
2. filtrationfiltered through Celite
3. customThe solvent was evaporated off under reduced pressure
4. dissolutionthe residue was dissolved in tetrahydrofuran (10 mL)
5. additionTo this, a saturated aqueous ammonium chloride solution was added
6. stirringthe mixture was stirred at room temperature for 30 minutes
7. extractionThen, extraction with ethyl acetate
8. washby washing with brine
9. dry with materialdrying over anhydrous sodium sulfate
10. customThe solvent was evaporated off under reduced pressure
11. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

ORD record

ord-7e7e582735fe47e1b28dc272202b3724

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673908B2