Efficient synthesis of tris(4-imidazolyl)methanol derivatives

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4301-4302

  Volkman, Jerome ^a   Nicholas, Kenneth M ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; METHANOL DERIVATIVE;

ARTICLE; CATALYSIS; SILYLATION; SOLVOLYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 9444247523     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048214z     Document Type: Article

References (20)

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13. 4, and the solvent was rotary evaporated. During evaporation, a white solid precipitated, which was filtered off and washed with ethyl acetate. The filtrate was concentrated, and the procedure was repeated to afford 2.19 g of spectroscopically pure 2 as a white solid (70% yield). Characterizational data for all compounds is provided in Supporting Information.
14. 4OH was used as the eluant, 362 mg of the neutral alcohol 3a was obtained (88% yield).
15. Preparative and characterizational information for compounds 2-6 is provided in Supporting Information.
16. Tagaki, W.; Ogino, K.; Fujita, T.; Yoshida, T.; Nishi, K.; Inaba, Y. Bull. Chem. Soc. Jpn. 1993, 66, 140. Wu, L.-P.; Yamagiwa, Y.; Ino, I.; Sugimoto, K.; Kuroda-Sowa, T.; Kamikawa, T.; Munakata, M. Polyhedron, 1999, 18, 2047. Gorun, S. M.; Lippard, S. J., J. Am. Chem. Soc. 1985, 107, 4568.
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19. O-Alkylation of other tris(imidazolyl) carbinols has proven to be erratic under typical base-promoted conditions. Sorrell, T. N.; Borovik, A. S. J. Am. Chem. Soc. 1987, 109, 4255. Collman, J. P.; Zhong, M.; Wang, Z.; Rapta. M. Org. Lett. 1999, 1, 2121.
20. O-Alkylation of other tris(imidazolyl) carbinols has proven to be erratic under typical base-promoted conditions. Sorrell, T. N.; Borovik, A. S. J. Am. Chem. Soc. 1987, 109, 4255. Collman, J. P.; Zhong, M.; Wang, Z.; Rapta. M. Org. Lett. 1999, 1, 2121.