Methyl 2-hydroxy-7-nitro-2,3-dihydrobenzofuran-4-carboxylate → Methyl 7-nitrobenzofuran-4-carboxylate

HRID 354053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354053
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[C:9]2[O:13][CH:12](O)[CH2:11][C:10]=12)=[O:4]>P(=O)(O)(O)O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[C:9]2[O:13][CH:12]=[CH:11][C:10]=12)=[O:4]

Komponenten

3

Edukt 1

HCID 20738652Methyl 2-hydroxy-7-nitro-2,3-dihydrobenzofuran-4-carboxylate

Produkt 1

HCID 20738655Methyl 7-nitrobenzofuran-4-carboxylateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1004Phosphoric AcidLösungsmittel

Versuchsvorschrift

2-Hydroxy-7-nitro-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester prepared above was heated in phosphoric acid (60 mL) at 100° C. for one hour. The reaction mixture was poured into ice water and the aqueous solution was extracted with ethyl acetate. The organic phase was washed with brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 15% ethyl acetate in hexane to give 7-nitro-benzofuran-4-carboxylic acid methyl ester as solid (2.3 g, 40%). 1H (CDCl3) δ: 4.04 (s, 3H), 7.54 (d, 1H, J=2.0 Hz), 7.95 (d, 1H, J=1.9 Hz), 8.07 (d, 1H, J=8.5 Hz), 8.17 (d, 1H, J=8.5 Hz).

Aufarbeitung

  1. extractionthe aqueous solution was extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography over silica gel eluting with 15% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-88add26b2b5b4de4a5f62bbe1580379c
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756395B2

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