Methyl morpholine oxide → HCID 57443292, compound

To a solution of 2-allyl-4-methyl-benzoic acid methyl ester (0.980 g, 5.15 mmol) in acetone (20 mL) and water (2.0 mL) are added N-methyl morpholine oxide (0.89 g, 7.57 mmol) and OsO4 (1 mg). The resulting reaction mixture is stirred at room temperature for three hours. The reaction mixture is diluted with ethyl acetate (50 mL) and is washed with Na2S2O3 (1.0 M, 20 mL). The organic layer are concentrated and the residue is dissolved in THF (25 mL) and water (15 mL). To the solution, NaIO4 (3.24 g, 15.2 mmol) is added and the mixture is stirred at room temperature for two hours. The mixture is filtered and the filtrate is concentrated, diluted with ethyl acetate (60 mL), and washed with Na2S2O3 (1.0 M, 20 mL). The organic layer is dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue is purified via flash chromatography eluting with 30-40% ethyl acetate in hexane to give the title compound (0.260 g, 26%). 1H NMR (400 MHz, CDCl3) δ 9.74 (s, 1H), 7.94-7.92 (d, 1H), 7.15-7.13 (d, 1H), 7.00 (s, 1H), 3.99 (s, 2H), 3.81 (s, 3H), 2.35 (s, 3H).

1. customThe resulting reaction mixture
2. washis washed with Na2S2O3 (1.0 M, 20 mL)
3. concentrationThe organic layer are concentrated
4. dissolutionthe residue is dissolved in THF (25 mL)
5. stirringthe mixture is stirred at room temperature for two hours
6. filtrationThe mixture is filtered
7. concentrationthe filtrate is concentrated
8. additiondiluted with ethyl acetate (60 mL)
9. washwashed with Na2S2O3 (1.0 M, 20 mL)
10. dry with materialThe organic layer is dried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customThe crude residue is purified via flash chromatography
14. washeluting with 30-40% ethyl acetate in hexane

ORD record

ord-8179b6e675314b40a7b61e81230afcf4

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846960B2