Quinone → (3,4-Dimethoxyphenyl)(5-hydroxybenzofuran-3-yl)methanone

HRID 1914791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914791
CN([CH:4]=[CH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:7])C.[C:18]1(=[O:25])[CH:23]=[CH:22][C:21](=[O:24])[CH:20]=[CH:19]1>C(O)(=O)C>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([C:6]([C:5]2[C:20]3[CH:19]=[C:18]([OH:25])[CH:23]=[CH:22][C:21]=3[O:24][CH:4]=2)=[O:7])[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Komponenten

4

Edukt 2

HCID 4650QuinoneHCID 1481361(E)-1-(3,4-dimethoxyphenyl)-3-(dimethylamino)-2-propen-1-one

Produkt 1

HCID 24152961(3,4-Dimethoxyphenyl)(5-hydroxybenzofuran-3-yl)methanoneAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A suspension of enaminone 12 (2 g, 8.43 mmol) and compound benzoquinone Q-4 (910 mg, 8.43 mmol) in acetic acid was stirred at room temperature under an atmosphere of N2 for 5 h. The precipitate that formed was filtered, washed with water, and dried under high vacuum to afford compound 13 (1.2 g, 47%) as an off-white solid. TLC Rf=0.5 (petroleum ether-EtOAc, 7:3); 1H NMR (DMSO-d6) δ 9.43 (s, 1H), 8.59 (s, 1H), 7.57-7.43 (band, 4H), 7.12 (d, J=8.3 Hz, 1H), 6.86 (dd, J=9.0 Hz, 2.6 Hz, 1H), 3.87 (s, 3H), 3.85 (s, 3H); MS (ES) m/z 299 (M+H)+.

Aufarbeitung

  1. customThe precipitate that formed
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fdb6c37a7ed145a3901a0f651005b44f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614237B2

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