Diisobutylaluminumhydride → Methyl 1-formylcyclohexane-1-carboxylate

HRID 2055188Notes

Reaction equation

HRID 2055188 reaction equation
[C:1]1([C:12]([O:14][CH3:15])=[O:13])([C:8]([O:10]C)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]C1.[H-].C([Al+]CC(C)C)C(C)C>C(OCC)C>[CH3:15][O:14][C:12]([C:1]1([CH:8]=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:13]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 64994993Dimethyl cycloheptane-1,1-dicarboxylate

Product 1

HCID 10866761Methyl 1-formylcyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of dimethyl cycloheptane-1,1-dicarboxylate (7.62 g, 35.6 mmol) in diethyl ether (250 mL) at −78° C. under an argon atmosphere was added diisobutylaluminum hydride (1.5M in toluene, 48 mL, 72 mmol) dropwise. After 1.5 h, the reaction mixture was quenched with a mixutre of methanol (100 mL) and water (100 mL), was filtered through Celite@ and was extracted with diethyl ether (100 mL×3). The combined organic extracts were dried (MgSO4), were filtered and were evaporated in vacuo to yield the title compound which was used without further purification. MH+185.

Workup

  1. customthe reaction mixture was quenched with a mixutre of methanol (100 mL) and water (100 mL)
  2. filtrationwas filtered through Celite@
  3. extractionwas extracted with diethyl ether (100 mL×3)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationwere filtered
  6. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-22552ffca0ac4d9099edd349d67cfdfc
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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