Diethyl Ether → HCID 23020430, compound

Under a nitrogen atmosphere, a 3.0M solution of methylmagnesium bromide in diethyl ether (3.7 ml, 11.1 mmol) was added dropwise over 5 minutes to a 1M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (22 ml, 22 mmol) at −50° C. (dry ice-acetone bath), followed by stirring as it was for 1 hour. Then, a solution of ethyl (E)-3-(2-furyl)-2-(4-pyridyl)-2-propenoate (2.4 g, 9.87 mmol) in tetrahydrofuran (20 ml) was added dropwise thereinto over 5 minutes. The reaction mixture was stirred for 30 minutes while elevating to room temperature, and then the reaction was terminated by adding hydrochloric acid. After diluting with a saturated aqueous ammonium chloride solution, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=1:1 to 4:1), to give the title compound (0.52 g, 23%).

1. waitover 5 minutes
2. stirringThe reaction mixture was stirred for 30 minutes
3. customwhile elevating to room temperature
4. customthe reaction was terminated
5. additionby adding hydrochloric acid
6. additionAfter diluting with a saturated aqueous ammonium chloride solution
7. extractionthe mixture was extracted with ethyl acetate
8. washThe organic layer was washed with brine
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated
11. washThe residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=1:1 to 4:1)

ORD record

ord-3a43b721bcb2451daf1b6a7f47defed9

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07396836B2