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CAS No. : | 16378-06-6 | MDL No. : | MFCD06655385 |
Formula : | C7H8O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YUSDDNTYMDWOCY-UHFFFAOYSA-N |
M.W : | 156.20 | Pubchem ID : | 268918 |
Synonyms : |
|
Chemical Name : | 3-(Thiophen-3-yl)propanoic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With methanesulfonic acid; phosphorus pentoxide; at 20℃; for 1h; | To a suspension of P2O5 (25.4 g, 179.0 mmol) in methanesulfonic acid (100 mL) was added 3-(thiophen-3-yl)propanoic acid (5.0 g, 32.0 mmol) and the reaction was stirred at room temperature for 1 h. At completion, the reaction was concentrated and the residue was purified by flash chromatography (20-30% EtOAc/hexane eluent) to give 4H-cyclopenta[b]thiophen-6(5H)-one (1.34 g, 30% yield) as a brown solid. 1H NMR (300 MHz, MeOH) delta ppm 8.14 (d, J=4.8 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 2.94-3.15 (m, 4H); MS (EI) m/z=139.2 [M+1]+. |
0.41 g | With phosphorus pentoxide; In methanesulfonic acid; at 20℃; for 1h; | Step iii: 4H-cyclopentarblthiophen-6(5H)-one To a 50 mL round bottom flask, were added phosphorous pentoxide (8.5 g, 0.0299 mol) and methanesulfonic acid (17 mL). To the same flask, 3-(thiophen-3-yl)propanoic acid (0.85 g, 0.0054 mol) was added. The reaction mixture was stirred at RT for 1 h. The reaction mixture was quenched with ice cold water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to get crude product. The crude product was purified by flash column chromatography using 30 % ethyl acetate in hexane to get the title compound [0.41 g, 55 %]. LC-MS: 139.1 [M+H]+. |
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