Ethyl Acetate → HCID 67080394, compound

Temperature

50 °C

To 7-fluoro-2,2-dimethyl-2,3-dihydrochromen-4-one (1.000 g, 5.149 mmol) was added trimethylsilyl cyanide (3.215 mL, 25.75 mmol) followed by a spatula tip of zinc iodide. The reaction was heated at 50° C. for 1 hour. The reaction was cooled, diluted with ethyl acetate (40 mL) and washed with saturated sodium bicarbonate (2×25 mL), brine (25 mL), dried over magnesium sulfate and concentrated. The product was dissolved in 5 mL of acetic acid and 5 mL of HCl, and SnCl2 dihydrate (4.648 g, 20.60 mmol) was added. The reaction heated at reflux (130° C. oil bath temperature) overnight. The reaction was cooled, diluted with ethyl acetate (50 mL), washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography over silica gel eluting with a gradient of 0.5% MeOH/CH2Cl2 containing 0.5% acetic acid to 10% MeOH/CH2Cl2 containing 0.5% acetic acid to provide the title compound (0.280 g, 24.25% yield).

1. temperatureThe reaction was cooled
2. washwashed with saturated sodium bicarbonate (2×25 mL), brine (25 mL)
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated
5. dissolutionThe product was dissolved in 5 mL of acetic acid
6. temperatureThe reaction heated
7. temperatureat reflux (130° C. oil bath temperature) overnight
8. temperatureThe reaction was cooled
9. washwashed with water (50 mL) and brine (50 mL)
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated
12. customThe residue was purified by silica gel chromatography over silica gel eluting with a gradient of 0.5% MeOH/CH2Cl2 containing 0.5% acetic acid to 10% MeOH/CH2Cl2 containing 0.5% acetic acid

ORD record

ord-150d4e245b7741a38f0706ab981a186d

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716498B2