Diisobutylaluminum hydride → 3-(4-Methoxyphenyl)propanal

Temperatur

-78 °C

3-(4-Methoxy-phenyl)-propionic acid (9a, 1.80 g, 10.0 mmol) in toluene (25.0 mL) was cooled to −78° C. in dry ice-acetone bath for 5-10 minutes under N2. DIBAL-H (11.0 mmol) was slowly added by syringe and stirred for 2 hours at −78° C. Then, the reaction mixture was poured quickly into an aqueous NH4Cl solution with vigorous stirring. The solution was extracted twice with ether and the organic layer was washed with brine, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide 3-(4-methoxy-phenyl)-propionaldehyde (9b, 1.16 g, 7.07 mmol) as yellow oil in 70.7% yield.

1. extractionThe solution was extracted twice with ether
2. washthe organic layer was washed with brine
3. dry with materialdried over MgSO4(s)
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by column chromatography on silica gel

ORD-Eintrag

ord-8b93349babcb42c493cc05b58688e64b

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08883793B2