2-Methylindole → 1-Benzyl-2-methylindole

HRID 5597

Reaktionsgleichung

Reaktionsgleichung von HRID 5597
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[K+]>O.C1(C)C=CC=CC=1>[CH2:11]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 3

HCID 72242-MethylindoleHCID 7503Benzyl ChlorideHCID 14797Potassium Hydroxide

Produkt 1

HCID 33071511-Benzyl-2-methylindoleAusbeute 9,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 13.11 g (0.1 mole) of 2-methylindole, 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 60° for 23 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 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine and dried over MgSO4. Evaporation of the solvent left 26.98 g of dark brown oil. The oil was chromatographed on a 1100 g column of silica gel. The column was eluted 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 20-22 were combined giving 2.08 g (9%) of 1-benzyl-2-methylindole as a yellow oil which solidified.

Aufarbeitung

  1. temperatureheated at 60° for 23 hours
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with 100 mL of toluene
  4. washThe combined toluene phases were washed 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 26.98 g of dark brown oil
  8. customThe oil was chromatographed on a 1100 g column of silica gel
  9. washThe column was eluted with 25% CH2Cl2 -Skellysolve B and 200 mL fractions
  10. customwere collected

Quellen und Nachweise

ORD-Eintrag
ord-1e9c28188ba44ba1b3e90f556b1d3cd8
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245046

Verknüpfte Notizen

Wird geladen…