Ammonium Chloride → HCID 86662730, compound

To a mixture of methyl 5-fluoro-3-(methoxymethyl)-1-benzofuran-2-carboxylate (5.01 g) synthesized above, calcium chloride (4.66 g), ethanol (50 mL) and tetrahydrofuran (50 mL) was added at 0° C. sodium borohydride (3.18 g), and the mixture was stirred at room temperature for 3 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, the organic solvent was evaporated in an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a colorless oil. To a mixture of the obtained oil, 4-methylmorpholine N-oxide (3.69 g) and acetonitrile (50 mL) was added tetrapropylammonium perruthenate (738 mg) at 0° C., and the mixture was stirred for 1.5 hr and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-20% ethyl acetate/hexane) to give the title object compound (2.33 g, 53%) as a pale-yellow solid.

1. customto quench
2. customthe reaction
3. customthe organic solvent was evaporated in an evaporator
4. extractionthe residue 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. customto give a colorless oil
9. stirringthe mixture was stirred for 1.5 hr
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (0-20% ethyl acetate/hexane)

ORD record

ord-427d099b32294a6b939ee45f654ea13f

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2