Sodium hydride → methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate

HRID 1427257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427257
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>CN(C=O)C.CCOC(C)=O>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH:15]([N:1]2[C:9]3[C:4](=[C:5]([CH:10]=[O:11])[CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[C:16]([O:18][CH3:19])=[O:17])=[CH:25][CH:24]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 333703Indole-4-carboxaldehydeHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetate

Produkt 1

HCID 86705047methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1H-indole-4-carbaldehyde (2.0 g, 13.79 mmol) in DMF (50 mL) was added NaH (0.66 g, 16.55 mmol) at 0° C. After stirring for 30 min at 0° C., a solution of methyl 2-bromo-2-(4-chlorophenyl)-acetate (4.67 g, 17.92 mmol) in DMF (20 mL) was added dropwise. The reaction was allowed to warm to rt and stirred for an additional 1 hr. Then it was diluted with EtOAc (200 mL) and quenched with water. The organic layer was separated and washed with brine (50 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was purified via column chromatography (0-20% EtOAc/hexanes) to provide the title compound.

Aufarbeitung

  1. temperatureto warm to rt
  2. stirringstirred for an additional 1 hr
  3. customquenched with water
  4. customThe organic layer was separated
  5. washwashed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe residue was purified via column chromatography (0-20% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8b48ad9519324559a723f178c789bb0c
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933113B2

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