Methyl 4-hydroxy-4-(5-indanyl)-2-butynoate → Methyl 3-(5-indanylcarbonyl)propiolate
Reaktionsgleichung
[OH:1][CH:2]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][CH2:13][CH2:12]2)[C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:14]1[C:15]2[C:11](=[CH:10][C:9]([C:2]([C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6])=[O:1])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of 6 g (26 mmol) of methyl 4-hydroxy-4-(5-indanyl)-2-butynoate in 200 ml of methylene chloride was added dropwise at 0° to a suspension of 68 g (0.78 mol) of manganese dioxide in 200 ml of methylene chloride. The reaction mixture was stirred at 0° for 20 minutes, filtered over magnesium sulphate and concentrated. The residue was purified by flash chromatography on 500 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1). There was obtained methyl 3-(5-indanylcarbonyl)propiolate as a yellow oil.