2-Iodothiophene → 1-(5-Iodothiophen-2-yl)propan-1-one

Temperature

-40 °C

38.4 ml of a 2M solution of lithium diisopropylamide (8.2 g, 76.8 mmol) in THF-heptane-ethylbenzene was added to THF (50 ml) taken in a 500 three neck RB flask equipped with a nitrogen inlet. The mixture was cooled to −40° C. and then 2-iodothiophene (16.1 g, 76.8 mmol) taken in 50 ml of THF was added with vigorous stirring. After 10 minutes the mixture was warmed to −10° C. and stirred for 30 min. The reaction mixture was re-cooled to −40° C. and N-methoxy-N-methylpropionamide (9 g, 76.8 mmol) taken in 50 ml of THF was added in one portion. The reaction mixture was allowed to warm slowly to 0° C. and then the reaction was quenched with saturated 50 ml of NH4Cl solution. The contents were extracted with 3×100 ml of DCM, dried over MgSO4 and concentrated to give an oily residue. This was purified by flash chromatography to give the title compound (10 g, 49%).

1. customequipped with a nitrogen inlet
2. additionwas added with vigorous stirring
3. temperatureAfter 10 minutes the mixture was warmed to −10° C.
4. temperatureThe reaction mixture was re-cooled to −40° C.
5. additionwas added in one portion
6. temperatureto warm slowly to 0° C.
7. customthe reaction was quenched with saturated 50 ml of NH4Cl solution
8. extractionThe contents were extracted with 3×100 ml of DCM
9. dry with materialdried over MgSO4
10. concentrationconcentrated
11. customto give an oily residue
12. customThis was purified by flash chromatography

ORD record

ord-12f9a54c101a4badadd4b53d949fe5ea

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853205B2