Triethylamine → 2-[2-[[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]-3-pyridyl]acetonitrile

To a mixture of [2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]-3-pyridyl]methanol (1.47 g), triethylamine (760 mg) and ethyl acetate (150 mL) was dropwise added methanesulfonyl chloride (860 mg) under ice-cooling and the mixture was stirred at room temperature or 2 hrs. The reaction mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated to give an oil. To a mixture of this oil and dimethyl sulfoxide (50 mL) was added an aqueous solution (5 mL) of sodium cyanide (280 mg) at room temperature and the mixture was stirred at room temperature for 12 hrs. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give crystals (1.40 g, 68%) of 2-[2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]-3-pyridyl]acetonitrile from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals (1.07 g, 71%). melting point: 110-111° C.

1. temperaturecooling
2. washThe reaction mixture was washed with water
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationconcentrated
5. customto give an oil
6. stirringthe mixture was stirred at room temperature for 12 hrs
7. extractionthe mixture was extracted with ethyl acetate
8. washThe ethyl acetate layer was washed with water
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated

ORD record

ord-dfafea64c7d14bdc818238683e1c549f

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238716B2