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

Temperature

0 °C

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.

1. stirringthe mixture was stirred at room temperature for 12 hr
2. concentrationThe reaction mixture was concentrated under reduced pressure, diethyl ether (200 ml)
3. additionwas added to the residue
4. stirringthe mixture was stirred
5. filtrationThe insoluble material (mainly triphenylphosphineoxide) was filtered
6. washwashed 4 times with diethyl ether (50 ml)
7. concentrationThe filtrate was concentrated under reduced pressure
8. customthe concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 450 g, ethyl acetate:hexane=1:6)

ORD record

ord-8b4f61b589034d83a11d569e95eab166

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507690B2