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

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%).

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 1 mol/L aqueous hydrogen chloride solution was added
6. stirringthe mixture was stirred at room temperature for 30 minutes
7. additionThe reaction was stopped by addition of a saturated aqueous sodium bicarbonate solution to the reaction mixture, and 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-d27b4244d52a490bb46927b59ffea633

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673908B2