Synthesis of 3-phenyl-3-hydroxy-4- l-acetoxyhexylidene tetrahydrofuran

Under a nitrogen atmosphere, 2-(2 -octynyloxy)-l-phenylethanone (1) (136 mg, 0.5 mmol) was added to a mixture of Pd(OAc)2 (5.6 mg, 0.025 mmol), 2,2 -bipyridine (4.5 mg, 0.030 mmol), HO Ac (1 mL), and 1,4-dioxane (4 mL). The solution was stirred at 80 °C for 14 hours until the reaction was complete as monitored by TLC. On cooling, the reaction mixture was neutralised with saturated sodium hydrogencarbonate, and then extracted with diethyl ether (3 x 20 mL). The combined ether solution was washed with saturated sodium chloride, dried with sodium sulfate and concentrated. The residue was purified by flash chromatography on silica gel (EtOAc/petroleum ether 1/4) to give the product 3-phenyl-3-hydroxy-4-(l -acetoxyhexylidene)tetrahydrofuran (2) in 80% yield as a white solid m.p. 79.5-80.5 °C. 

2 SYNTHESIS OF DIMETHYL 3-ACETYL AMINO-4-BUTYRYLCYCLOPENT-3-ENE-1,1-DICARBOXYLATE (4) 

METAL CATALYSED CARBON-CARBON BOND-FORMING REACTIONS 

The present catalytic reactions can be performed even in an atmosphere of oxygen/moisture due to the stability of Pd(OAc)/bpy. 

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