Diisobutylaluminum hydride → HCID 58443665, compound

Temperature

-60 °C

To a stirred solution N-methoxy-N-methyl-3-(2,4,6-trichloro-phenyl)-propionamide (0.9 g, 3.04 mmol) in toluene (18 mL), DIBAL-H (15.2 mL, 15.2 mmol) was added at −60° C. slowly in drops over a period of 20 minutes and the reaction mass was stirred at −60° C. for 3 hours. Reaction mass was then quenched with dil. HCl (20 ml) in drops, followed by dilution with water (10 ml) and stirred for 15 minutes. Toluene layer was separated and resulting aqueous phase was extracted with ethyl acetate (30 mL×3). The combined organic layer was washed with water and brine. The organic layer was then dried over anhydrous sodium sulphate and concentrated under reduced pressure. The resulting crude mass was purified over column chromatography (silica gel 60-120 mesh, 2% ethyl acetate in hexane) to afford white crystalline solid of 3-(2,4,6-trichloro-phenyl)-propionaldehyde (0.45 g, 62.5%)

1. customReaction mass
2. customwas then quenched with dil. HCl (20 ml) in drops
3. stirringstirred for 15 minutes
4. customToluene layer was separated
5. customresulting aqueous phase
6. extractionwas extracted with ethyl acetate (30 mL×3)
7. washThe combined organic layer was washed with water and brine
8. dry with materialThe organic layer was then dried over anhydrous sodium sulphate
9. concentrationconcentrated under reduced pressure
10. customThe resulting crude mass was purified over column chromatography (silica gel 60-120 mesh, 2% ethyl acetate in hexane)

ORD record

ord-f18bb8a1ed8f4fdf94d2618ea3d6e4f1

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258169B2