Reaktion #456320

Reaktionsgleichung

methylmagnesium iodide

ethyl 4-phenylbenzoylformate

3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

→

5-[(1,1'-biphenyl)-4-yl]-3-phenylmethoxy-4-hydroxy-5-methyl-2(5H)-furanone

Ausbeute 30.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give

Vorschrift

A total of 3.4 mL (10.2 mmol) of 3.0M methylmagnesium iodide in THF was added to a THF solution of 2.4 g (10 mmol) of ethyl 4-phenylbenzoylformate in an analogous manner as described for the synthesis of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to give prior to hydrogenolysis, 1.1 g (30% yield) of 5-[(1,1'-biphenyl)-4-yl]-3-phenylmethoxy-4-hydroxy-5-methyl-2(5H)-furanone as a white granular solid: m.p. 182-183° C. (benzene/hexanes) 1H NMR (CDCl3) δ 7.56-7.26 (m, 14H), 5.10 (ab quartet, 2H, J=11.4 Hz), 1.79 (s, 3H). 13C NMR (CDCl3) δ 168.5, 163.8, 141.5, 140.3, 137.0, 136.3, 129.0, 128.8, 128.8, 128.8, 127.6, 127.2, 127.1, 125.6, 119.0, 81.1, 73.5, 24.3. Anal Calcd for C24H20O4 : C, 77.40; H, 5.41. Found: C, 77.99; H, 5.61.

Quelle