Methyl 4-dimethylaminovinyl-3-nitrobenzoate → Methyl 4-formyl-3-nitrobenzoate

HRID 50363

Reaktionsgleichung

Reaktionsgleichung von HRID 50363
CN(C)C=[CH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16].I([O-])(=O)(=O)=[O:20].[Na+]>O1CCCC1.O.O.C(Cl)Cl>[CH:4]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])=[O:20]

Komponenten

6

Edukt 2

HCID 894336Methyl 4-dimethylaminovinyl-3-nitrobenzoateHCID 23667635Sodium periodate

Produkt 1

HCID 3457222Methyl 4-formyl-3-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

1.2 g (4.8 mmol) of methyl 4-(2-dimethylaminovinyl)-3-nitrobenzoate were dissolved in 120 mL of tetrahydrofuran/water (1:1) and after the addition of 3.0 g (14.3 mmol) of sodium metaperiodate the mixture was stirred for 20 hours at ambient temperature. The suspension was then diluted with water and methylene chloride and extracted with methylene chloride. The combined organic extracts were washed with sodium hydrogen carbonate solution, dried, and evaporated down. The residue was chromatographed on silica gel and eluted with ethyl acetate/cyclohexane (1:3). Yield: 0.6 g (63% of theory); Rf value: 0.63 (silica gel, ethyl acetate/cyclohexane=1:1).

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts were washed with sodium hydrogen carbonate solution
  3. customdried
  4. customevaporated down
  5. customThe residue was chromatographed on silica gel
  6. washeluted with ethyl acetate/cyclohexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-f6d982671ef64b3e8ae0bbc2d85e2e0b
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710055B2

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