Diisobutylaluminum hydride → 4-Methoxycyclohexane-1-carbaldehyde

Temperature

-78 °C

Into a 100-mL 3-neck round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of ethyl 4-methoxycyclohexane-1-carboxylate (1.3 g, 6.98 mmol) in dichloromethane (30 mL). This was followed by the addition of DIBAL-H (1 M in hexanes) (9 mL, 9 mmol) dropwise at −78° C. The reaction mixture was stirred for 3 h at −78° C., then quenched with 10 mL of NH4Cl (sat.). The aqueous phase was extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with 3×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. This resulted in 1 g (crude) of the title compound as a colorless oil.

1. customInto a 100-mL 3-neck round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. customquenched with 10 mL of NH4Cl (sat.)
4. extractionThe aqueous phase was extracted with 3×50 mL of ethyl acetate
5. washThe combined organic layers were washed with 3×50 mL of brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-07e98d6d615748e48a4b7c3c109671c0

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2