DOI QR코드

DOI QR Code

Oxidation of Benzylic Alcohols with Urea Hydrogen Peroxide/Calcium Chloride in PEGDME250

  • 투고 : 2013.08.01
  • 심사 : 2013.11.09
  • 발행 : 2014.02.20

초록

키워드

Experimental

All the alcohols and PEGDME250 were purchased from Aldrich and used as received. The reactions were checked by TLC using silica gel plates. Merck silica gel 60 (230-400 mesh) was used for flash column chromatography. 1H NMRspectra were measured by the Varian Gemini 2000 (300MHz) spectrometer tetramethylsilane as an internal standard and CDCl3 as a solvent. Mass spectra were recorded with a Micromass Autospectrometer. All products were known and identified by comparison of their 1H NMR spectra with those of reported literature data.

General Procedure. A mixture of benzylic alcohol (1.0 mmol), urea hydrogen peroxide (1.5 mmol) and calcium chloride (0.5 mmol) was stirred in PEGDME250 (2 mL) at 70 oC for 4 h. After cooling the mixture to room temperature the product is extracted into diethyl ether (3 × 20 mL), washed with water and dried over MgSO4. The combined ether extracts were concentrated under reduced pressure and the crude product was purified by flash column chromatography (ethyl acetate/n-hexane = 1:3, v/v) to give the desired carbonyl compound.

참고문헌

  1. Tojo, G.; Fernandez, M., Eds., Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice; Springer: Berlin, 2006.
  2. Shaabani, A.; Mirzaei, P.; Naderi, S.; Lee, D. G. Tetrahedron Lett. 2004, 60, 11415. https://doi.org/10.1016/j.tet.2004.09.087
  3. Cosner, C. C.; Cabrera, P. J.; Byrd, K. M.; Adams Thomas, A. M.; Helquist, P. Org. Lett. 2011, 13, 2071. https://doi.org/10.1021/ol200441g
  4. Shen, S.-S.; Kartika, V.; Tan, Y. S.; Webster, R. D. Narasaka, K. Tetrahedron Lett. 2012, 53, 986. https://doi.org/10.1016/j.tetlet.2011.12.058
  5. Lei, M.; Hu, R.-J.; Wang, Y.-G. Tetrahedron 2006, 62, 8928. https://doi.org/10.1016/j.tet.2006.07.022
  6. Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173. https://doi.org/10.1021/ol005792g
  7. Schultz, M. J.; Alder, R. S.; Zierkiewicz, W.; Privalov, T.; Sigman, M. S. J. Am. Chem. Soc. 2005, 127, 8499. https://doi.org/10.1021/ja050949r
  8. Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. J. Org. Chem. 1998, 63, 1750. https://doi.org/10.1021/jo971965c
  9. Jiang, B.; Feng, Y.; Ison, E. A. J. Am. Chem. Soc. 2008, 130, 14462. https://doi.org/10.1021/ja8049595
  10. Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1998, 39, 5323. https://doi.org/10.1016/S0040-4039(98)00987-3
  11. Jiang, N.; Ragauskas, A. J. J. Org. Chem. 2006, 71, 7087. https://doi.org/10.1021/jo060837y
  12. Sawyer, D. T.; Sobkowiak, A.; Matsushita, T. Acc. Chem. Res. 1996, 29, 409. https://doi.org/10.1021/ar950031c
  13. Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066. https://doi.org/10.1021/ja00123a008
  14. Shabani, A.; Lee, D. G. Tetrahedron Lett. 2001, 42, 5833. https://doi.org/10.1016/S0040-4039(01)01129-7
  15. Mardani, H. R.; Golchoubian, H. Tetrahedron Lett. 2006, 47, 2349. https://doi.org/10.1016/j.tetlet.2006.02.007
  16. Ni, J.; Yu, W.-J.; He, L.; Sun, H.; Cao, Y.; He, H.-Y.; Fan, K.-N. Green Chem. 2009, 11, 756. https://doi.org/10.1039/b820197h
  17. Varma, R. S.; Naicker, K. P. Org. Lett. 1999, 2, 189.
  18. Cooper, M. S.; Heaney, H.; Newbold, A. J.; Sanderson, W. R. Synlett 1990, 533.
  19. Heaney, H.; Newbold, A. J. Tetrahedron Lett. 2001, 42, 6607. https://doi.org/10.1016/S0040-4039(01)01332-6
  20. Pavlinac, J.; Zupan, M.; Stavber, S. Org. Biomol. Chem. 2007, 5, 699. https://doi.org/10.1039/b614819k
  21. Filipan-Litvi , M.; Litvi , M.; Vinkovi , V. Tetrahedron 2008, 64, 5649. https://doi.org/10.1016/j.tet.2008.04.040
  22. Lehtimaa, T.; Kuitunen, S.; Tarvo, V.; Vuorinen, T. Ind. Eng. Chem. Res. 2010, 49, 2688. https://doi.org/10.1021/ie9018885

피인용 문헌

  1. . vol.45, pp.34, 2014, https://doi.org/10.1002/chin.201434040
  2. Synthesis of benzoquinoline derivatives from formyl naphthylamines via Friedländer annulation under metal-free conditions vol.149, pp.11, 2018, https://doi.org/10.1007/s00706-018-2268-x
  3. Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen vol.11, pp.23, 2014, https://doi.org/10.1039/d1ra02007b