Water → Methyl-4-(4-oxo-4H-chromen-3-ylmethyl)-benzoate

HRID 736489

Reaktionsgleichung

Reaktionsgleichung von HRID 736489
O.[O:2]=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH2:5][C:4]1=[CH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1>CCO.C(OCC)(=O)C>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([CH2:13][C:4]2[C:3](=[O:2])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][CH:5]=2)=[CH:15][CH:16]=1

Komponenten

5

Edukt 2

HCID 962WaterHCID 4240115Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate

Produkt 1

HCID 22478819Methyl-4-(4-oxo-4H-chromen-3-ylmethyl)-benzoateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Water (0.2 ml) and RhCl3.H2O (7 mg, 0.034 mmol) was added to a suspension of compound 260 (200 mg, 0.680 mmol) in EtOH (2 ml) and CDCl3 (2 ml). The reaction mixture was stirred 16 h at 70° C. The reaction mixture was cooled down and diluted in ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (0.5-1% MeOH/CH2Cl2)to afford the title compound 261 (118 mg, 59%) as a white solid. 1H NMR: (DMSO) δ (ppm): 8.45 (s, 1H), 8.03 (dd, J=7.9, 1.8 Hz, 1H), 7.87 (d, J=8.4 Hz, 2H), 7.83-7.77(m, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.50-7.43 (m3, 1H), 3.82 (s, 3H), 3.80 (s, 2H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was then purified by flash chromatography on silica gel (0.5-1% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-de7c46c57cc946d98a53df9edb6631ff
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595343B2

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