Acetaldehyde → Ethyl 5-bromo-2-(1-hydroxyethyl)thiophene-3-carboxylate

Ethyl 2,5-dibromothiophene-3-carboxylate (22.3 g) synthesized above was dissolved in tetrahydrofuran (200 mL), and 1.0M isopropylmagnesium bromide-tetrahydrofuran solution (78.0 mL) was added dropwise at −45° C. After stirring under an argon atmosphere for 1 hr, acetaldehyde (19.9 mL) was added dropwise, and the mixture was stirred at −45° C. for 1 hr, and at room temperature for 2 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio) to give the title compound (9.63 g, 49%) as a yellow oil.

1. stirringthe mixture was stirred at −45° C. for 1 hr
2. waitat room temperature for 2 hr
3. customto quench
4. customthe reaction
5. extractionthe mixture was extracted with ethyl acetate
6. washThe extract was washed with brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio)

ORD record

ord-62f62f6b1d40428daefa932ff894a609

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309580B2