Diazomethane → HCID 22235737, Verbindung

Reaktionsgleichung

[CH3:1][C:2](=[CH2:10])[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[N+](=[CH2:13])=[N-]>CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:10][C:2]1([CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:13][CH2:1]1

Komponenten

Versuchsvorschrift

To an ice cold solution of ethyl 4-methyl-4-pentenoate (1.11 g, 7.8 mmol) in 0.5 M diazomethane in Et2O, was added palladium(II) acetate by portionwise addition (4 portions of 5 mg each were added in 15 min intervals). A total of 4 portions were added. The reaction mixture was filtered on a pad of celite and concentrated under 60 mm Hg with gentle warming. This crude product was treated a second time with diazomethane and palladium(II) acetate, filtered and concentrated. The resulting oil was filtered on a pad of florisil (60–100 mesh), washed with Et2O (2×10 mL), concentrated under 60 mm Hg to give ethyl 3-(1-methylcyclopropyl)propanoate as a colorless oil.