Diisobutylaluminum hydride → 4-Methoxycyclohexane-1-carbaldehyde
Reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9](OCC)=[O:10])[CH2:5][CH2:4]1.CC(C[AlH]CC(C)C)C>ClCCl>[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]=[O:10])[CH2:5][CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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.