2-Methoxyethanol → HCID 66779368, compound

To a solution (25 mL) of 2-methoxyethanol (2.74 mL) in N,N-dimethylformamide was added sodium hydride (60%, oily, 835 mg) at 0° C., and the mixture was stirred at room temperature for 30 min. After stirring, a solution (25 mL) of methyl 3-(bromomethyl)-5-fluoro-1-benzofuran-2-carboxylate (5.00 g) synthesized in Example A47(2) in N,N-dimethylformamide was added at 0° C. The reaction mixture was stirred at 80° C. for 5 hr, then saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-40% ethyl acetate/hexane) to give the title object compound (1.54 g, 31%) as a pale-yellow oil.

1. stirringAfter stirring
2. additionwas added at 0° C
3. stirringThe reaction mixture was stirred at 80° C. for 5 hr
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (0-40% ethyl acetate/hexane)

ORD record

ord-25fba18c9db74ea5a4cb29d5ca2ac35e

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2