Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl (2E)-3-[4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophen-2-yl]acrylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophene-2-carbaldehyde (12.82 g, 50.00 mmol) in chloroform (128 ml) was added methyl (triphenyl phosphanylidene)acetate (17.55 g, 52.50 mmol) at 0° C. by small portions. After stirring at 0° C. for 1 hr, the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, diethyl ether (200 ml) was added to the residue, and the mixture was stirred. The insoluble material (mainly triphenylphosphineoxide) was filtered, and washed 4 times with diethyl ether (50 ml). The filtrate was concentrated under reduced pressure, and the concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 450 g, ethyl acetate:hexane=1:6) to give methyl (2E)-3-[4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophen-2-yl]acrylate (13.76 g, 44.04 mmol, yield 88.1%) as a pale-yellow oil.

Provenance & Evidence