Reaktion #2142385

Reaktionsgleichung

3-butyl-cyclobutane-1,1-dicarboxylic acid dimethyl ester

diisobutylaluminum hydride

→

title compound

3-Butyl-1-Formyl-Cyclobutanecarboxylic Acid Methyl Ester

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was quenched with saturated aqueous NH4Cl solution (150 mL)
2. 2
   ExtraktionThe aqueous phase was extracted with diethyl ether (100 mL×5)
3. 3
   Trocknenwas dried (MgSO4)
4. 4
   Sonstigewas evaporated in vacuo

Vorschrift

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.

Quelle