6-Vinyl-1H-indole-3-carbaldehyde → 6-Ethyl-1H-indole-3-carbaldehyde

HRID 1527164

Reaktionsgleichung

Reaktionsgleichung von HRID 1527164
[CH:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH:12]=[O:13])=[CH:8][NH:9]2)=[CH:5][CH:4]=1)=[CH2:2]>C1COCC1.[Pd]>[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH:12]=[O:13])=[CH:8][NH:9]2)=[CH:5][CH:4]=1)[CH3:2]

Komponenten

4

Edukt 1

HCID 866737896-Vinyl-1H-indole-3-carbaldehyde

Produkt 1

HCID 218501566-Ethyl-1H-indole-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Vinyl-1H-indole-3-carbaldehyde (1.5 g, 8.76 mmol) was dissolved in THF (45 mL), Pd/C 10% (300 mg) was added and the solution was degassed 3 times replacing air by nitrogen and finally nitrogen by hydrogen. The reaction mixture was further stirred under hydrogen atmosphere 4 h and the catalyst was removed through a pad of Celite and washed with THF. The solvent was concentrated under and the crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1) to give the desired compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.40; MS (LC/MS): 174.1 [M+H]+, 196.1 [M+Na]+, 172.1 [M−H]−; tR (HPLC conditions a): 3.05 min.

Aufarbeitung

  1. customthe solution was degassed 3 times
  2. customthe catalyst was removed through a pad of Celite
  3. washwashed with THF
  4. concentrationThe solvent was concentrated under and the crude residue
  5. customwas purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-45295aa9039b495e9b9c4000aa41cd3a
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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