Methanol → Methyl 3-(4-hydroxyphenyl)-2-methoxypropanoate
Reaktionsgleichung
[N+](=[C:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5])=[N-].[CH3:16][OH:17]>CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH:3]([O:17][CH3:16])[C:4]([O:6][CH3:7])=[O:5])=[CH:10][CH:11]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of methyl 2-diazo-3-(4-hydroxyphenyl)propanoate (cf Tetrahedron Lett., 1971, 4495) (8.58 g) in methanol (120 mL) was added over 10 minutes to a mixture of rhodium (II) acetate dimer (0.18 g) in methanol (50 mL) at room temperature under a nitrogen atmosphere. The resulting mixture was heated at reflux for 5 hrs, allowed to stand at room temperature for 15 hrs, then concentrated in vacuo. The residue was dissolved in ethyl acetate (500 mL), washed with water (3×300 mL) and brine (500 mL), dried (MgSO4) and evaporated. The resulting gum was chromatographed on silica gel with a gradient of 4% ethyl acetate to 6% ethyl acetate in dichloromethane as eluent to afford the title compound. mp 61°-3° C.