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CAS No. : | 1006-68-4 | MDL No. : | MFCD00067074 |
Formula : | C9H7NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YPYPBEGIASEWKA-UHFFFAOYSA-N |
M.W : | 145.16 | Pubchem ID : | 589311 |
Synonyms : |
|
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: |
* 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 |
---|---|---|
90.9% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; Stage #2: With hexachloroethane In tetrahydrofuran at 25℃; for 12 h; |
[0819] to a solution of 5-phenyloxazole (800 mg, 5.51 mmol) in THF (10 ml) was added n-BuLi (2.5 m, 2.76 ml) drop-wise at -78 °C and stirred for 30 min, then hexachloroethane (1.96 g, 8.27 mmol) in THF (2 ml) was added, the reaction mixture was slowly warmed to 25 °C and stirred for 12 h. The mixture was poured into ice- water (20 ml) and extracted ethyl acetate (10 ml x 2), the organic phases were washed with brine (10 ml), dried over Na2SO4, filtered and concentrated, the residue was purified by silica gel column (petroleum ether: ethyl acetate = 10: 1) to give 114a (900 mg, yield: 90.9percent) as yellow oil. 1H NMR (400mhz, CDCl3) δ 7.58 (d, = 7.3 hz, 2h), 7.45 - 7.38 (m, 2h), 7.38 - 7.31 (m, 1h), 7.27 (s, 1h). |
49% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.25 h; Stage #2: With hexachloroethane In tetrahydrofuran at -78 - 20℃; for 2 h; |
[00208] To a round bottom flask was added 5-phenyloxazole (1.0 gm, 6.89 mmol) and THF (10 mL). The reaction was cooled to -78 °C. Then 2.5 M nBuLi (3.03 mL, 7.58 mmol) was added to the reaction at -78 °C. The reaction turned to deep red color. After 15 min, hexachloroethane (1.170 mL, 10.33 mmol) was added at -78 °C. The reaction was slowly warmed to rt over 2 hrs and then was poured onto ice. The resulting solution was extracted with EtO Ac (2 x 30ml). The combined EtO Ac layers were washed with saturated aqueous NaCl, dried over MgS04, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100percent EtO Ac/Hex to give the product, 2-chloro-5-phenyloxazole, (600 mg, 3.34 mmol, 49 percent yield) as a light pale liquid. Anal. Calcd. for C9H6C1N0 m/z 179.1, found: 180.1 (M+H)+; 'H NMR (500 MHz, CDC13) δ ppm 7.60 (d, J=7.15 Hz, 2 H), 7.43 (t, J=7.42 Hz, 2 H), 7.38 - 7.33 (m, 1 H), 7.29 (s, 1 H); 13C NMR (126 MHz, CDCl3) 5 ppm 153.78, 146.16, 129.01, 126.93, 124.03, 123.31. |
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