Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl (2E)-3-(4-hydroxy-1-benzothiophen-7-yl)prop-2-enoate

Temperature

120 °C

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 4-hydroxy-1-benzothiophene-7-carbaldehyde (168 mg, 0.85 mmol, 1.00 equiv, 90%), Ethyl (triphenylphosphoranylidene)acetate (493 mg, 1.42 mmol, 1.50 equiv), Tolune (6 mL). The resulting solution was stirred for 4 h at 120° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 5 mL of H2O. The resulting solution was extracted with 3×5 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1×10 mL of sodium chloride(aq). The mixture was dried over anhydrous sodium sulfate. The residue was purified by thin layer chromatography developed with ethyl acetate/petroleum ether (1:8). This resulted in 200 mg (81%) of ethyl (2E)-3-(4-hydroxy-1-benzothiophen-7-yl)prop-2-enoate as brown oil.

1. customInto a 50-mL 3-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. concentrationThe resulting mixture was concentrated under vacuum
4. additionThe resulting solution was diluted with 5 mL of H2O
5. extractionThe resulting solution was extracted with 3×5 mL of ethyl acetate
6. washThe resulting mixture was washed with 1×10 mL of sodium chloride(aq)
7. dry with materialThe mixture was dried over anhydrous sodium sulfate
8. customThe residue was purified by thin layer chromatography
9. customThis resulted in 200 mg (81%) of ethyl (2E)-3-(4-hydroxy-1-benzothiophen-7-yl)prop-2-enoate as brown oil

ORD record

ord-00c643771dc141ddb22a960eb0dea839

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1