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5-Benzyloxyindole → 5-Benzyloxy-3-(3-carbomethoxybenzoyl)indole

HRID 129698
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 129698
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Mg]Br.[C:21]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29])([O:23][CH3:24])=[O:22]>O1CCCC1.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:28](=[O:29])[C:27]1[CH:31]=[CH:32][CH:33]=[C:25]([C:21]([O:23][CH3:24])=[O:22])[CH:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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Komponenten

6

Edukt 3

HCID 146245-BenzyloxyindoleHCID 15563901Methyl 3-(chlorocarbonyl)benzoateHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 193722425-Benzyloxy-3-(3-carbomethoxybenzoyl)indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a solution 5-benzyloxyindole (2.23 g, 10 mmol) in 5 ml of tetrahydrofuran (THF), cooled in an external ice bath, is added dropwise with stirring 6.15 ml of a 2 molar solution of methyl magnesium bromide in diethyl ether. The resulting mixture is stirred for an additional 15 minutes in the ice bath and a solution of 3-carbmethoxybenzoyl chloride in 10 ml of THF is added dropwise. The cooling bath is removed and the reaction mixture is stirred at room temperature for 18 hours. Water is then added, followed by ethyl acetate. The layers are separated. The organic layer is dried (MgSO4) and concentrated in vacuo. The residue obtained is purified by a silica gel column, eluting with a solvent system of 25% ethyl acetate in hexane to give 5-benzyloxy-3-(3-carbomethoxybenzoyl)indole. NMR confirms this structure.

Aufarbeitung

  1. additionis added dropwise
  2. customThe cooling bath is removed
  3. additionWater is then added
  4. customThe layers are separated
  5. dry with materialThe organic layer is dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained
  8. customis purified by a silica gel column
  9. washeluting with a solvent system of 25% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-2edc6501a1ca4230900e7f76e6b0942e
Quelldatensatz
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05468898

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