Potassium Carbonate → (1-Methyl-1H-indol-7-yloxy)-acetic acid ethyl ester

HRID 1009017

Reaktionsgleichung

Reaktionsgleichung von HRID 1009017
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3]1.I[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:2]([CH3:1])[CH:3]=[CH:4]2)[CH3:18]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12183Ethyl iodoacetateHCID 221368021-methyl-1H-indol-7-ol

Produkt 1

HCID 67304817(1-Methyl-1H-indol-7-yloxy)-acetic acid ethyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-methyl-1-H-indol-7-ol (Chemstep, CAS: 47577-334, 2.5 g, 17 mmol) and ethyl iodoacetate (Fluka, CAS: 623-48-3, 4.58 g, 21 mmol) in DMF abs. (25 mL) was added potassium carbonate (4.23 g, 31 mmol). The reaction mixture was stirred at rt for 20 h, quenched with ice/water, and extracted with ethyl acetate. The organics were washed, dried and concentrated, the residue was chromatographed on silica gel using heptanelethyl acetate as eluent to obtain the desired compound (3.37 g) as a creamy solid. MS (ISP): m/e 234.1 (M+H)+

Aufarbeitung

  1. customquenched with ice/water
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was chromatographed on silica gel using heptanelethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-a31fab5e8e3c47a8838aa07a1e1c47f2
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973051B2

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