Hydrogen Peroxide → 4-nitro-2,3-dihydro-1H-inden-2-yl acetate

Temperatur

0 °C

To a solution of 2,3-dimethyl-2-butene (21.5 mg, 0.31 mmol) in THF (2 ml) at 0° C. was added borane-THF (0.307 ml, 0.31 mmol) dropwise. After stirred for 1 hour at 0° C., 7-nitro-1H-indene (45.0 mg, 0.28 mmol) in THF (5 ml) was added dropwise, and the mixture was stirred for 2 hours at ambient temperature. The mixture was cooled to 0° C., and water (0.15 ml), 4N aqueous sodium hydroxide (0.45 ml), and 30% H2O2 (0.45 ml) were added. The mixture was then warmed to room temperature and poured into water, extracted with ethyl acetate and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. To the obtained mixture in toluene (1 ml) was added acetic anhydride (40.8 mg, 0.40 mmol) and pyridine (0.4 ml), and then stirred for 16 hours at room temperature. The mixture was concentrated under reduced pressure, and the obtained residue was purified by preparatory TLC (hexane:ethylacetate 2:1) to obtain 4-nitro-2,3-dihydro-1H-inden-2-yl acetate (16.0 mg).

1. stirringthe mixture was stirred for 2 hours at ambient temperature
2. temperatureThe mixture was cooled to 0° C.
3. temperatureThe mixture was then warmed to room temperature
4. extractionextracted with ethyl acetate
5. washwashed with brine
6. dry with materialThe organic layer was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. stirringstirred for 16 hours at room temperature
10. concentrationThe mixture was concentrated under reduced pressure
11. customthe obtained residue was purified by preparatory TLC (hexane:ethylacetate 2:1)

ORD-Eintrag

ord-554be209bdd74171846f39b6ffcba9eb

Quelldatensatz

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07615557B2