Reaktion #5691

Reaktionsgleichung

2-phenylindole

benzyl chloride

KOH

→

1-benzyl-2-phenylindole

Ausbeute 13.2%

Lösungsmittel

H2O

toluene

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated at 55°-60° for 24 hours
2. 2
   SonstigeThe layers were separated
3. 3
   ExtraktionThe aqueous layer was extracted with 100 mL of toluene
4. 4
   WaschenThe combined toluene phases were washed with 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine
5. 5
   Trocknendried over MgSO4
6. 6
   SonstigeEvaporation of the solvent
7. 7
   workup.WAITleft 32.3 g of dark brown oil
8. 8
   SonstigeThe oil was chromatographed on a 1100 g column of silica gel
9. 9
   Sonstigewere collected

Vorschrift

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.

Quelle