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

HRID 2055203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2055203
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-942e0f3865bf4dae91336ed209aaf127
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07332485B2

Notizen zur Reaktion

Wird geladen…