Diisobutylaluminumhydride → Methyl 1-formyl-4,4-dimethylcyclohexane-1-carboxylate
Reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][CH2:6][C:5]([C:12](OC)=[O:13])([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.[H-].C([Al+]CC(C)C)C(C)C>C(OCC)C>[CH3:11][O:10][C:8]([C:5]1([CH:12]=[O:13])[CH2:6][CH2:7][C:2]([CH3:16])([CH3:1])[CH2:3][CH2:4]1)=[O:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of dimethyl 4,4-dimethyl-cyclohexane-1,1-dicarboxylate (5.23 g, 22.9 mmol) in diethyl ether (250 mL) at −78° C. under a nitrogen atmosphere was added diisobutylaluminum hydride (1.5M in toluene, 30.6 mL, 45.9 mmol) dropwise. After 2.5 h, the reaction mixture was quenched with a mixture of methanol (75 mL) and water (75 mL). The mixture was filtered through Celite@ and the aqueous phase was extracted with diethyl ether (100 mL×5), was dried (MgSO4) and was evaporated in vacuo to yield the title compound which was used without further purification. MH+199.
Workup
- customthe reaction mixture was quenched with a mixture of methanol (75 mL) and water (75 mL)
- filtrationThe mixture was filtered through Celite@
- extractionthe aqueous phase was extracted with diethyl ether (100 mL×5)
- dry with materialwas dried (MgSO4)
- customwas evaporated in vacuo
Sources & evidence
- ORD record
- ord-d14ccf4292bc4635b289ced3704b87ae
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07332485B2
Reaction notes
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