Tetrahydrofuran → 1-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridine

HRID 907444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907444
[CH2:1]1[CH2:5]OC[CH2:2]1.I[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9]C=1.CCCC[N+:17]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19]CC.[F-]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:26]([N:17]1[CH2:18][CH:19]=[C:24]([C:25]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:7]=2)[CH2:23][CH2:22]1)[C:27]1[CH:28]=[CH:29][CH:5]=[CH:1][CH:2]=1

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 11575IodobenzeneHCID 2724141Tetrabutylammonium Fluoride

Produkt 1

HCID 5636091-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)KatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a 4-mL vial, added 100 mg (0.28 mmol) (7) and 6 mg (0.0058 mmol) Pd2dba3-CHCl3. Next added 0.3 mL THF, 48 μL (0.43 mmol) iodobenzene, and finally 1.1 mL (1.1 mmol) TBAF solution (1M in THF). Let stir at room temperature for 18 hours. At the end of the reaction, added 200 μL triethylamine, let stir briefly, concentrated in vacuo, and purified the crude material directly by silica gel chromatography (automated column, 12 g SiO2, 0% to 20% EtOAc in hexanes gradient). Obtained 63 mg (90%) of 1-Benzyl-4-phenyl-1,2,3,6-tetrahydro-pyridine as a yellow oil.

Aufarbeitung

  1. customAt the end of the reaction
  2. stirringlet stir briefly
  3. concentrationconcentrated in vacuo
  4. custompurified the crude material directly by silica gel chromatography (automated column, 12 g SiO2, 0% to 20% EtOAc in hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-3202a8b2dbaf489a80ace91b344e8e53
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013157B2

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