Benzyl Chloride → 1-Benzyl-2-phenyl-1H-indole

HRID 5595

Reaktionsgleichung

Reaktionsgleichung von HRID 5595
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[K+]>O.C1(C)C=CC=CC=1>[CH2:16]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 3

HCID 7503Benzyl ChlorideHCID 136982-PhenylindoleHCID 14797Potassium Hydroxide

Produkt 1

HCID 117480441-Benzyl-2-phenyl-1H-indoleAusbeute 13,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 19.33 g (0.1 mole) of 2-phenylindole, 13.92 g (0.11 mole) of benzyl chloride, 33 g (0.5 mole) of 85% KOH, 14 mL of H2O, 2.5 g (2.5 mmoles) of PEG-1000, and 100 mL of toluene was stirred and heated at 55°-60° for 24 hours. After cooling to room temperature, 100 mL of H2O was added. The layers were separated. The aqueous layer was extracted with 100 mL of toluene. The combined toluene phases were washed with 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine and dried over MgSO4. Evaporation of the solvent left 32.3 g of dark brown oil. The oil was chromatographed on a 1100 g column of silica gel. The column was elut4d with 25% CH2Cl2 -Skellysolve B and 200 mL fractions were collected. The fractions were assayed by silica gel tlc (1×4") (25% CH2Cl2 -Skellysolve B). Fractions 18-20 were combined giving 3.74 g (13%) of 1-benzyl-2-phenylindole as a solid.

Aufarbeitung

  1. temperatureheated at 55°-60° for 24 hours
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with 100 mL of toluene
  4. washThe combined toluene phases were washed with 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent
  7. waitleft 32.3 g of dark brown oil
  8. customThe oil was chromatographed on a 1100 g column of silica gel
  9. customwere collected

Quellen und Nachweise

ORD-Eintrag
ord-3ef121dbf1f0400b85825dd9302cc9ce
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245046

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