Alternatived Products of [ 156780-52-8 ]
Product Details of [ 156780-52-8 ]
CAS No. : | 156780-52-8 |
MDL No. : | MFCD19347420 |
Formula : |
C10H9NO2
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
175.18
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 156780-52-8 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 156780-52-8 ]
* 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.
- Downstream synthetic route of [ 156780-52-8 ]
- 1
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[ 288-42-6 ]
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[ 696-62-8 ]
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[ 156780-52-8 ]
Yield | Reaction Conditions | Operation in experiment |
90% |
Stage #1: oxazol With zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: para-iodoanisole With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 25℃; for 6h; Inert atmosphere; Schlenk technique; regioselective reaction; |
|
86% |
Stage #1: oxazol With n-butyllithium; zinc(II) chloride In tetrahydrofuran; hexane at -78 - 20℃;
Stage #2: para-iodoanisole In tetrahydrofuran at 60℃; for 4h; Further stages.; |
|
79% |
Stage #1: oxazol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: With zinc dibromide at -78 - 20℃;
Stage #3: para-iodoanisole With tetrakis(triphenylphosphine) palladium(0) at 60℃; for 0.5h; |
2-(4-Methoxyphenyl)oxazole(16)
To a solution of oxazole (178 L, 2.80 mmol) in THF (10 mL) was added dropwise n-BuLi (2.69 M sol. in n-hexane, 1.25 mL, 3.36 mmol) at -78 °C. After stirring for0.5 h at -78 °C, the resulting solution was treated with ZnBr2 (1.35g, 6.00 mmol) and warmed up to rt. p-Iodoanisole(468 mg, 2.00 mmol) and Pd(PPh3)4 (231 mg, 0.200 mmol)was added to the reaction mixture and stirred for 0.5 h at 60 °C. The reaction was quenched with a saturated aqueous NH4Cl solution and diluted with EtOAc. After removal of the organic layer, the aqueous layer was extracted with EtOAc. The organic layer was combined, washedwith H2O, dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography(8:1 hexanes/EtOAc) afforded 2-(4-methoxyphenyl)oxazole (16)(322 mg, 79%) as a pale yellow solid |
74% |
With copper(l) iodide In N,N-dimethyl-formamide at 140℃; for 74h; |
|
63% |
With potassium phosphate In 1-methyl-pyrrolidin-2-one at 125℃; for 36h; |
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23% |
With copper(l) iodide In N,N-dimethyl-formamide at 140℃; for 48h; |
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Reference:
[1]Haas, Diana; Mosrin, Marc; Knochel, Paul
[Organic Letters, 2013, vol. 15, # 24, p. 6162 - 6165]
[2]Ohnmacht, Stephan A.; Mamone, Patrizia; Culshaw, Andrew J.; Greaney, Michael F.
[Chemical Communications, 2008, # 10, p. 1241 - 1243]
[3]Yamamuro, Daisuke; Uchida, Ryuji; Ohtawa, Masaki; Arima, Shiho; Futamura, Yushi; Katane, Masumi; Homma, Hiroshi; Nagamitsu, Tohru; Osada, Hiroyuki; Tomoda, Hiroshi
[Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 2, p. 313 - 316]
[4]Bellina, Fabio; Calandri, Chiara; Cauteruccio, Silvia; Rossi, Renzo
[Tetrahedron, 2007, vol. 63, # 9, p. 1970 - 1980]
[5]Nandurkar, Nitin S.; Bhanushali, Mayur J.; Bhor, Malhari D.; Bhanage, Bhalchandra M.
[Tetrahedron Letters, 2008, vol. 49, # 6, p. 1045 - 1048]
[6]Bellina, Fabio; Cauteruccio, Silvia; Rossi, Renzo
[European Journal of Organic Chemistry, 2006, # 6, p. 1379 - 1382]
- 2
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[ 288-42-6 ]
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[ 213596-33-9 ]
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[ 156780-52-8 ]
- 3
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[ 156780-52-8 ]
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[ 288-42-6 ]
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[ 623-00-7 ]
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4-(2-(4-methoxyphenyl)oxazol-5-yl)benzonitrile
[ No CAS ]
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[ 87150-13-8 ]