Dimethylformamide → 5-(Phenylsulfanyl)thiophene-2-carbaldehyde

Temperature

-30 °C

To a solution of 2-phenylthiothiophene (3.87 g) in dry tetrahydrofuran (50 ml) at -30° C. under N2, was added dropwise, n-butyllithium (8.0 ml, 2.5M) and the solution left to stir at -30° C. for 2 hours. Dry dimethylformamide (2.32 ml) was then added and the solution allowed to stir at -30° C. for a further hour, allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched with 2N HCl (50 ml), extracted with ether (2×50 ml), dried over MgSO4 and evaporated under reduced pressure to give an orange oil. The oil was flash chromatographed on a Sorbsil C60-40/60H column using 20% ether-hexane to give a pale yellow oil.

1. stirringto stir at -30° C. for a further hour
2. temperatureto warm to room temperature
3. stirringstirred overnight
4. customThe reaction mixture was quenched with 2N HCl (50 ml)
5. extractionextracted with ether (2×50 ml)
6. dry with materialdried over MgSO4
7. customevaporated under reduced pressure
8. customto give an orange oil
9. customchromatographed on a Sorbsil
10. customto give a pale yellow oil

ORD record

ord-ac79734f41724f358df7da9819c3e0d4

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05158971