反应详情

温度

80 °C

To an oven-dried 250 mL flask under a nitrogen atmosphere was added anhydrous MeOH (200 mL). Na metal (1.07 g, 44 mmol) was weighed to a small beaker containing hexane and then transferred to the reaction vessel. After dissolution of the sodium, 3-cyanomethyl-pyridine-2-carbonitrile (5.3 g, 37 mmol) dissolved in anhydrous MeOH (10 mL) was added to the reaction. The resulting solution was heated at 80° C. for 3 hours, then stirred at room temperature overnight. The reaction mixture was concentrated to remove MeOH and extracted into CH2Cl2 (2×200 mL). The organic phases were combined, dried over Na2SO4, filtered, concentrated and unsuccessfully chromatographed (2% MeOH/CH2Cl2). The mixed fractions were combined and recrystalized from EtOAc/hexane affording 1.16 g (18%) of the title compound as a yellow solid. The mother liquor was rechromatographed (50% EtOAc/hexanes) to afford an additional 560 mg (9%) of product: mp decomposes above 110° C.; MS(+)APCI m/z 176 [M+H]+.

1. additionwas added to the reaction
2. concentrationThe reaction mixture was concentrated
3. customto remove MeOH
4. extractionextracted into CH2Cl2 (2×200 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customunsuccessfully chromatographed (2% MeOH/CH2Cl2)
9. customrecrystalized from EtOAc/hexane affording 1.16 g (18%) of the title compound as a yellow solid
10. customThe mother liquor was rechromatographed (50% EtOAc/hexanes)