Dimethyl cyclopentane-1,1-dicarboxylate → Methyl 1-formylcyclopentanecarboxylate

HRID 2055164Notes

Reaction equation

HRID 2055164 reaction equation
[C:1]1([C:10](OC)=[O:11])([C:6]([O:8][CH3:9])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH3:9][O:8][C:6]([C:1]1([CH:10]=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1)=[O:7]

Participants

4

Reactant 2

HCID 12609605Dimethyl cyclopentane-1,1-dicarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10931680Methyl 1-formylcyclopentanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of dimethyl cyclopentane-1,1-dicarboxylate (7.1 g, 38.1 mmol) in dichloromethane(75 mL) at −78° C. under an nitrogen atmosphere was added diisobutylaluminum hydride (1.5M in toluene, 51 mL, 76 mmol) dropwise. After 4 h, the reaction mixture was quenched with saturated aqueous NH4Cl solution (30 mL), then 1N HCl (38 mL) and allowed to warm to room temperature. The mixture was filtered through Celite@ and the organic phase was separated, was dried (MgSO4) and was evaporated in vacuo to yield the title compound which was used without further purification (3.1 g, 52%). MH+157.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl solution (30 mL)
  2. filtrationThe mixture was filtered through Celite@
  3. customthe organic phase was separated
  4. dry with materialwas dried (MgSO4)
  5. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-9f81dfb3f6114fad83ee35458542aab2
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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