1-Methylimidazole → HCID 59031741, compound

To a solution (50 mL) of ethyl acetate containing 2,2,8-trimethyl-7-nitro-2H-1-benzopyran (3.32 g, 15.1 mmol), N-methyl imidazole (0.482 mL, 6.05 mmol) and (R,R,S,S)-Ph,Ph salen manganese complex (XY) (142 mg, 0.151 mmol) were added at room temperature, and sodium hypochlorite aqueous solution (34.1 mL, 1.776 mol/kg, 60.5 mmol) was added dropwise, and the resulting mixture was stirred at room temperature for 1 hour. Upon the completion of the reaction, sodium thiosulfate aqueous solution was added to the reaction solution, the resulting solution was filtered through celite. The resulting filtrate extracted with ethyl acetate. The organic phase was washed with water and sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=7/1) and the aimed product was obtained as pale yellow crystal (yield: 78%, optical purity: 99% ee).

1. additionwere added at room temperature
2. additionwas added to the reaction solution
3. filtrationthe resulting solution was filtered through celite
4. extractionThe resulting filtrate extracted with ethyl acetate
5. washThe organic phase was washed with water and sodium chloride aqueous solution
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationAfter distilling off the solvent
8. customthe residue was purified by column chromatography (hexane/ethyl acetate=7/1)

ORD record

ord-b0a1d4787b69411184243abdf1fcc4c4

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07781483B2