Dimethylformamide → 4-Ethylthiophene-2-carbaldehyde

To a solution of 3-ethylthiophene (2 g, 17.7 mmol) in ether (20 ml) under N2 at room temp is added butyl lithium, 2.5M in hexane solution (8.15 ml, 21.4 mmol) and the resulting straw coloured solution is heated to reflux for 20 minutes. The resulting cloudy solution is then cooled to room temperature before the slow addition of DMF (2 ml) over 2 minutes and the resulting solution is stirred at room temp for 1 hour. The reaction is quenched with aqueous saturated ammonium chloride (100 ml) and extracted with chloroform (100 ml). The organic layer is washed with brine, dried over magnesium sulphate and concentrated to give 4-ethyl thiophene-2-carbaldehyde as a light brown oil (2.48 g).

1. temperatureis heated
2. temperatureto reflux for 20 minutes
3. customThe reaction is quenched with aqueous saturated ammonium chloride (100 ml)
4. extractionextracted with chloroform (100 ml)
5. washThe organic layer is washed with brine
6. dry with materialdried over magnesium sulphate
7. concentrationconcentrated

ORD record

ord-98eda48fe59f481aaf5cf66c19a16d1c

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530667B2