Réaction #65932

Équation de réaction

3-Dipropylamino-5-aminochroman

2,5-dimethoxytetrahydrofuran

NaOH

→

title compound

3-Dipropylamino-5-(pyrrol-1-yl)chroman

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   TempératureThe solution was refluxed for 1 hour
2. 2
   Extractionextracted with toluene
3. 3
   SéchageThe organic phase was dried with sodium sulfate
4. 4
   Autreevaporated to dryness
5. 5
   AutreThe residue was purified by flash chromatography on silica gel by elution with ethyl acetate/hexane 1:9

Mode opératoire

3-Dipropylamino-5-aminochroman (Example 14; 0.60 g, 2.42 mmol) was dissolved in acetic acid (10 ml) and 2,5-dimethoxytetrahydrofuran (0.40 g, 3.0 mmol) was added. The solution was refluxed for 1 hour. The solution was neutralized with NaOH (aq.) and extracted with toluene. The organic phase was dried with sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel by elution with ethyl acetate/hexane 1:9 to give the title compound. 13C-NMR: 111.75 21.89 24.81 52.69 53.15 67.94 108.93 115.67 118.22 118.44 121.87 127.22 141.47 155.27.

Source