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CAS No. : | 931-49-7 | MDL No. : | MFCD00001568 |
Formula : | C8H10 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | DKFHWNGVMWFBJE-UHFFFAOYSA-N |
M.W : | 106.17 | Pubchem ID : | 79128 |
Synonyms : |
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Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P233-P241-P242-P243-P261-P280-P303+P361+P353-P305+P351+P338 | UN#: | 3295 |
Hazard Statements: | H225-H315-H319-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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 |
---|---|---|
> 99% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In acetonitrile; at 20℃;Inert atmosphere; | General procedure: <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> (100.0 mg, 0.38 mmol, 1.0 equiv) in CH3CN (5.0 mL) was added sequentially with PdCl2(PPh3)2 (5.4 mg, 0.01 mmol, 0.02 equiv), Ph3P (4.0 mg, 0.02 mmol, 0.04equiv), 1-chloro-4-ethynylbenzene (57.6 mg, 0.42 mmol, 1.1 equiv). The resulting solution was degassed by passing through a steady stream of argon for 30 min (flask 1). In the meantime in another flask, a mixture of CuI (3.0 mg, 0.02 mmol, 0.04 equiv) in Et3N was also degassed bypassing through a steady stream of argon for 30 min (flask 2). After degassing, the mixture ofCuI in Et3N in flask 2 was transferred into the solution in flask 1 using a syringe with wide-boarneedle which resulted in the reaction solution turning yellow and giving white precipitates. The reaction mixture was allowed to stir at room temperature overnight and was quenched byaddition with sat. aq. NH4Cl. The separated aqueous phase was extracted with EtOAc (3x times).The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30-50% EtOAc-hexane to yield 114.6 mg of compound 1d (>99%)as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
154 mg | With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 80℃; for 3h;Inert atmosphere; | General procedure: To a solution of 2-disubstituted 1-methyl-1H-imidazole 1 (1 mmol) in DMF (5 mL), NBS(169 mg, 0,95 mmol) was added and the resulting reaction mixture was stirred in the dark at room temperature for 3h. Then, Pd(PPh3)2Cl2 (14 mg, 0.02 mmol, 2 mol%), CuI (8 mg, 0.04mmol, 4 mol%), an alkyne 3 (1,1 mmol) and piperidine (300 muL, 255 mg, 3 mmol) were added and the resulting reaction mixture was stirred at 80C (when trimethylsilylacetylene was employed as the alkyne, the reaction was carried out at 50C) for 3 h. The reaction mixture was diluted with EtOAc (100 mL), then saturated aqueous NH4Cl (100 mL) was added. The resulting mixture was stirred for 30 minutes and extracted with EtOAc (3x 25mL). The organic extracts were washed with water (3 x 25 mL) and brine (1 x 25 mL), driedover anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatogaraphy on silica gel. This procedure was employed to prepare compounds 4a-l. GLC analysis showed that all these compounds had chemical purity higherthan 98%. |
[ 210829-14-4 ]
1-Ethynyl-2-(hex-1-yn-1-yl)cyclopent-1-ene
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