Iodoethane → 2-(4-chlorophenyl)-1-ethyl-3-methyl-1H-pyrrole

Temperature

0 °C

A solution of 2-(4-chlorophenyl)-3-methyl-1H-pyrrole (prepared according to the procedure given in Tetrahedron Letters 46 (2005) 4539-4542, 1.0 g, 5.22 mmol) in DMF (10 ml) was added dropwise to a stirred suspension of Sodium hydride (0.23 g, 5.74 mmol, 60% dispersion in mineral oil) in 20 ml DMF at 0° C. under a nitrogen atmosphere. The reaction mixture was then stirred at about 0° C. for 30 min. Ethyl iodide (0.89 g, 0.47 ml, 5.74 mmol) was then added to the reaction mixture maintaining the temperature at 0° C. The reaction mixture was then stirred at 25° C. for 3 hrs. The progress of the reaction was monitored by TLC. The reaction mixture was slowly quenched with cold water (30 ml) and the resulting mixture was then extracted with ethyl acetate (2×30 ml). The combined organic layer was then washed with brine (1× 30 ml) and dried over sodium sulfate. The dried organic layer was then concentrated under reduced pressure to obtain crude product as semi-solid mass (0.8 g), which was then purified by flash column chromatography using 5% ethyl acetate in hexanes as an eluent to obtain the title compound (0.6 g, 52.3%).

1. temperaturemaintaining the temperature at 0° C
2. stirringThe reaction mixture was then stirred at 25° C. for 3 hrs
3. customThe reaction mixture was slowly quenched with cold water (30 ml)
4. extractionthe resulting mixture was then extracted with ethyl acetate (2×30 ml)
5. washThe combined organic layer was then washed with brine (1× 30 ml)
6. dry with materialdried over sodium sulfate
7. concentrationThe dried organic layer was then concentrated under reduced pressure
8. customto obtain crude product as semi-solid mass (0.8 g), which
9. customwas then purified by flash column chromatography

ORD record

ord-f4d0789fa5814a15bf2c9e10c0a0dfaf

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09072731B2