Tetrahydrofuran → 5-(2-hydroxyethyl)-2-benzofuran-1(3H)-one

5-allyl-2-benzofuran-1(3H)-one (1.53 g, 8.78 mmol) was dissolved in methanol (30 mL). THF was added to solubilize the starting material. The resulting mixture was cooled in a dry ice acetone bath (−78° C.) and ozone was bubbled into the reaction until the color of the mixture changed to orange. Nitrogen was bubbled into the reaction for one minute to remove the excess ozone. Sodium borohydride (0.65 g, 2.9 mmol) was added at −78° C., and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was concentrated part way and then taken up in ethyl acetate and water. The layers were separated and the organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to provide 5-(2-hydroxyethyl)-2-benzofuran-1(3H)-one. 1H NMR (500 MHz, CD3OD) δ 7.77 (m, 1H), 7.37-7.41 (m, 2H), 5.23 (s, 2H), 3.92 (m, 2H), 2.99 (m, 2H).

1. customwas bubbled into the reaction until the color of the mixture
2. customNitrogen was bubbled into the reaction for one minute
3. customto remove the excess ozone
4. concentrationThe reaction mixture was concentrated part way
5. customThe layers were separated
6. washthe organic layer was washed with brine
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-094519690a444cb4a6a3b87ed183883e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073882B2