Diisobutylaluminumhydride → Methyl 3-butyl-1-formylcyclobutane-1-carboxylate

HRID 2055203Notes

Reaction equation

HRID 2055203 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:13](OC)=[O:14])[CH2:8][CH:7]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:6]1)=[O:4].[H-].C([Al+]CC(C)C)C(C)C>C(OCC)C>[CH3:1][O:2][C:3]([C:5]1([CH:13]=[O:14])[CH2:6][CH:7]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:8]1)=[O:4]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 69222797Dimethyl 3-butylcyclobutane-1,1-dicarboxylate

Product 1

HCID 71416977Methyl 3-butyl-1-formylcyclobutane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-butyl-cyclobutane-1,1-dicarboxylic acid dimethyl ester (8.37 g, 36.7 mmol) in diethyl ether (300 mL) at −78° C. under a nitrogen atmosphere was added diisobutylaluminum hydride (1.5M in toluene, 49 mL, 73.4 mmol) dropwise. After 2.5 h, the reaction mixture was quenched with saturated aqueous NH4Cl solution (150 mL) then with 1N HCl solution (150 mL). The aqueous phase was extracted with diethyl ether (100 mL×5), was dried (MgSO4) and was evaporated in vacuo to yield the title compound as a clear, colorless oil (7.2 g, 100%) which was used without further purification. MH+199.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl solution (150 mL)
  2. extractionThe aqueous phase was extracted with diethyl ether (100 mL×5)
  3. dry with materialwas dried (MgSO4)
  4. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-942e0f3865bf4dae91336ed209aaf127
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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