Reaktion #1254627

Reaktionsgleichung

chlorotriphenylmethane

Triethylamine

triethylamine

Trimethylsilyl chloride

3-(4-Imidazolyl)propionic acid

→

desired product

Ausbeute 82.9%

3-(1-Triphenylmethyl-4-imidazolyl)propionic Acid

Ausbeute 82.9%

Lösungsmittel

dichloromethane

MeOH

dichloromethane

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture refluxed for 4 hours
2. 2
   Temperaturrefluxing
3. 3
   TemperaturCooled
4. 4
   workup.STIRRINGthe mixture stirred for 30 minutes
5. 5
   Sonstigeevaporated to dryness
6. 6
   workup.ADDITIONWater (50 ml) was added to the residue
7. 7
   FiltrationThe precipitate was filtered off
8. 8
   Waschenwashed with diethyl ether
9. 9
   Sonstigedried

Vorschrift

3-(4-Imidazolyl)propionic acid (1.0 g, 7.1 mmol) was suspended in a mixture of dichloromethane (5 ml) and acetonitrile (25 ml). Trimethylsilyl chloride (781 mg, 7.2 nmmol) was added and the mixture refluxed for 4 hours. Triethylamine (1 ml) was added, and refluxing continued for 15 minutes. Cooled, triethylamine (1 ml) added followed by chlorotriphenylmethane (1.99 g, 7.1 mmol) in dichloromethane (10 ml), and the mixture stirred at ambient temperature for 2 hours. MeOH (20 ml) was added, the mixture stirred for 30 minutes, then evaporated to dryness. Water (50 ml) was added to the residue, and the pH adjusted to 8-8.5 with triethylamine. The precipitate was filtered off, washed with diethyl ether, and dried to give the desired product (2.25 g). MS (ESP): 383 (MH+) for C25H22N2O2;

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