Reaktion #1696579

Reaktionsgleichung

1-methylindole-3glyoxylic acid

pentafluorophenol

acetic acid

dicyclohexylcarbodiimide

→

pentafluorophenyl 1-methylindole-3-glyoxylate

Ausbeute 22.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   workup.WAITleft
3. 3
   workup.WAITto stand for 60 hours
4. 4
   Sonstigethe mixture obtained
5. 5
   Filtrationwas filtered
6. 6
   EinengenThe filtrate was concentrated under reduced pressure
7. 7
   SonstigeThe residue was purified by flash chromatography on silica gel
8. 8
   Waschenfor the elution

Vorschrift

1.13 g (5.5 mol) of dicyclohexylcarbodiimide were added to a solution, cooled in ice, of 1 g (5 mmol) of 1-methylindole-3glyoxylic acid and 1.01 g (5 mmol) of pentafluorophenol in 50 ml of dry tetrahydrofuran. After stirring for 4 hours under a nitrogen atmosphere at 0° C., the mixture was allowed to warm to room temperature and left to stand for 60 hours. Then, 3 ml of glacial acetic acid were added and the mixture obtained was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using dichloromethane for the elution to give 404 mg (22%) of pentafluorophenyl 1-methylindole-3-glyoxylate in the form of a pale yellow solid of melting point 168°-9° C.

Quelle