Undec-4-ene → 4-(azidomethyl)-1H-indole

HRID 393009

Reaktionsgleichung

Reaktionsgleichung von HRID 393009
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH2:10]O)[C:4]=2[CH:3]=[CH:2]1.C1(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)C=CC=CC=1.CCCCCCC=CCCC>O1CCCC1>[N:26]([CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2)=[N+:27]=[N-:28]

Komponenten

5

Edukt 3

HCID 136496Undec-4-eneHCID 199401P,P-Diphenylphosphinic azideHCID 27734571H-indol-4-ylmethanol

Produkt 1

HCID 226613274-(azidomethyl)-1H-indoleAusbeute 1.810,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1H-indole-4-methanol (71 mg, 0.48 mmol) in tetrahydrofuran (1 mL) at 0° C. was added diphenylphosphoryl azide (156 μL, 0.72 mmol) followed by 1,8-diaza[5.4.0]undec-7-ene (87.4 μL, 0.58 mmol). The cooling bath was removed and the solution was allowed to stir for 5 h. The solvent was evaporated and ethyl acetate was added. The solution was washed with 1 M HCl and brine, dried (MgSO4), filtered, concentrated and chromatographed (12% ethyl acetate/hexanes) to give 4-(azidomethyl)-1H-indole (1.496 g, 88%) as an oil.

Aufarbeitung

  1. customThe cooling bath was removed
  2. customThe solvent was evaporated
  3. additionethyl acetate was added
  4. washThe solution was washed with 1 M HCl and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (12% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-655cc2b235f04d2eb70d4b678afdbf13
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803384B2

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