Acetyl chloride → 4-(3-Bromo-4,5-dimethoxyphenyl)-2-methoxy-7-methyl-pyrrolo[2,3-h]chroman

HRID 1454003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454003
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[C:17]4[CH:24]=[CH:23][N:22]([CH3:25])[C:18]4=[CH:19][CH:20]=3)[O:15][CH:14]([OH:26])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].[C:27](Cl)(=O)C.C(=O)(O)[O-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[C:17]4[CH:24]=[CH:23][N:22]([CH3:25])[C:18]4=[CH:19][CH:20]=3)[O:15][CH:14]([O:26][CH3:27])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 103872724-(3-Bromo-4,5-dimethoxyphenyl)-2-hydroxy-7-methyl-pyrrolo[2,3-h]chroman

Produkt 1

HCID 100028974-(3-Bromo-4,5-dimethoxyphenyl)-2-methoxy-7-methyl-pyrrolo[2,3-h]chromanAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(3-bromo-4,5-dimethoxyphenyl)-2-hydroxy-7-methyl-pyrrolo[2,3-h]chroman (5 mg; 0.012 mmol ) in methanol (0.5 ml) at 0° C. was added acetyl chloride (10 μl). The mixture was warmed to room temperature and stirred at this temperature for 3 h. Saturated sodium bicarbonate solution was added and the reaction mixture was extracted with dichloromethane. The extract was washed with saturated sodium chloride solution, dried and evaporated. The crude product was passed through bond-elute (hexane:ethyl acetate=9:1 as eluent), giving the title compound (3 mg; 58%). 1H NMR (acetone-d6): 7.14 (d, J=2.7 Hz) and 7.13 (d, J=2.9 Hz) (1H), 6.94-7.02 (m, 2H), 6.89 and 6.88 (d each, J=8.5 Hz, 1H), 6.50-6.57 (m, 2H), 5.32 (t, J=2.6 Hz) and 5.27 (dd, J=2.3, 7.6 Hz) (1H), 4.34 (dd, J=6.6, 9.5 Hz) and 4.27 (dd, J=6.0, 11.3 Hz) (1H), 3.85, 3.82, 3.81, 3.80, 3.79, 3.78 (s each, 9H), 3.59 and 3.50 (s each, 3H), 2.43 (ddd, J=2.3, 6.6, 13.3 Hz) and 2.12-2.30 (m) (2H).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washThe extract was washed with saturated sodium chloride solution
  3. customdried
  4. customevaporated
  5. washthrough bond-elute (hexane:ethyl acetate=9:1 as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-549057ea24964e55abfab53bb3a9c267
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476741B2

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