Tetrahydrofuran → 2-(Thiophen-2-yl)benzaldehyde

Temperature

-20 °C

To a solution of 3-bromothiophene (30 mmol) in tetrahydrofuran (20 mL) at -78° C. under nitrogen was added dropwise n-butyllithium in hexane (30 mmol). The mixture was stirred for 45 minutes and magnesium bromide etherate (45 mmol) was added portionwise. The reaction mixture was then allowed to warm to -20° C. over 45 minutes. This mixture was added to a suspension of di-μ-acetato-bis[2-(N-phenylformimidoyl)phenyl]dipalladium (15 mmol) [Onoue et al., J. Organometallic Chem., 43, pp. 431-436 (1972)] and triphenylphosphine (60 mmol) in benzene (250 mL) and the reaction mixture stirred at ambient temperature overnight. The cooled reaction mixture was quenched with 1N hydrochloric acid (175 mL), was stirred for 2.5 hours, filtered, and the phases separated. The aqueous phase was extracted with diethyl ether (2×150 mL) and the combined organic phases were washed with brine and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo to give an oil which was purified by flash chromatography on silica gel eluted with ethyl acetate:hexane (3:97) to yield Compound 1a as an oil (Rf =0.4).

1. customThe cooled reaction mixture
2. customwas quenched with 1N hydrochloric acid (175 mL)
3. stirringwas stirred for 2.5 hours
4. filtrationfiltered
5. customthe phases separated
6. extractionThe aqueous phase was extracted with diethyl ether (2×150 mL)
7. washthe combined organic phases were washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationAfter filtration
10. customthe solvent was removed in vacuo
11. customto give an oil which
12. customwas purified by flash chromatography on silica gel
13. washeluted with ethyl acetate:hexane (3:97)

ORD record

ord-a1bc63e4ee6c4e1185369881485d3102

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04599341