6-Nitroveratraldehyde → HCID 178487640, compound

4,5-Dimethoxy-2-nitrobenzaldehyde (1.52 g, 7.19 mmol), 353.0 mg (6.07 mmol) of potassium fluoride, and 134.8 mg (0.59 mmol) of benzyltriethylammonium chloride were added to a solution of 1.51 g (5.97 mmol) of phenylthio(trimethylsilyl)methyl isothiocyanate, synthesized according to a document (J. Chem. Soc., Perkin Trans 1 1984, 435.), in acetonitrile (36 ml), and the mixture was stirred at room temperature overnight. The solvent was removed from the reaction solution by distillation, and the water and chloroform were then added to the residue. The aqueous layer was extracted with chloroform. The organic layer was washed with saturated brine and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1→1:1) to give 302.4 mg (yield 18%) of the title compound.

1. customsynthesized
2. customThe solvent was removed from the reaction solution by distillation
3. additionthe water and chloroform were then added to the residue
4. extractionThe aqueous layer was extracted with chloroform
5. washThe organic layer was washed with saturated brine
6. dry with materialwas then dried over anhydrous sodium sulfate
7. customThe solvent was removed by distillation
8. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1→1:1)

ORD record

ord-28be155f82dd4f2bb9d6b853b28f3c64

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07867980B2