Water → HCID 67403470, compound

4-Methoxymethoxybenzaldehyde (658 mg, 3.96 mmol) was dissolved in tetrahydrofuran (4.0 mL). To this, (trifluoromethyl)trimethylsilane (702 μL, 475 mmol) and tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 396 μL, 0.396 mmol) were added under a nitrogen atmosphere at 0° C. and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 4.00 mL, 4.00 mmol) was added and the mixture was further stirred for 10 minutes. After water was added to the reaction mixture, 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=7/3) to give 1-methoxymethoxy-4-(2,2,2-trifluoro-1-hydroxyethyl)benzene (Compound CQ) (895 mg, yield: 96%).

1. stirringthe mixture was further stirred for 10 minutes
2. washby washing with brine
3. dry with materialdrying over anhydrous sodium sulfate
4. customThe solvent was evaporated off under reduced pressure
5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)

ORD record

ord-c410e1c8944f4aceaec27561f69355e7

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673908B2