Preparation of diphenylmethyl esters by Oxone® oxidation of benzophenone hydrazone

Tetrahedron Letters

Volumn 38, Issue 7, 1997, Pages 1239-1240

  Curini, Massimo ^a   Rosati, Ornelio ^a   Pisani, Emanuela ^a   Cabri, Walter ^b   Brusco, Stefano ^b   Riscazzi, Massimiliano ^b  

^a UNIVERSITY OF PERUGIA   (Italy)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZHYDRYL DERIVATIVE; ESTER;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0031575627     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00046-4     Document Type: Article

References (10)

1. 1. a) Stelakatos, G. C.; Paganou, A.; Zervas, L. J. Chem. Soc., Perkin C 1966, 1191-1199;
2. b) Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley and Sons, Inc.: New York, 1991, pp. 253-254.
3. 2. a) Hishey, R. G.; Adams, Jr., J. B. J. Am. Chem. Soc. 1965, 87, 3969-3973;
4. b) Lapatsanis, L. Tetrahedron Lett. 1978, 4697-4698;
5. c) Lapatsanis, L.; Milias, G.; Paraskewas, S. Synthesis 1985, 513-515;
6. d) Fraussios, C.; Kolovos, M. Synthesis 1987, 1106-1108.
7. 3. a) Bywood, R.; Gallagher, G.; Sharma, G. K.; Walker, D. J. Chem Soc. Perkin 1 1975, 2019-2022;
8. b) Kametani, T.; Sekine, H.; Honda, T. Chem. Pharm. Bull. 1982, 30, 4545-4547.
9. 4. For the preparation of wet Alumina see: Greeenhalgh, R. P. Synlett 1992, 235-236.
10. 5. Experimental procedure: to a solution of starting material (2 mmol) in dichloromethane (10 ml) benzophenone hydrazone (3.2 mmol) was added at 0° C. After addition of 1% (w/w) iodine in dichloromethane solution (0.1 ml) a mixture of wet Alumina (2.28 g) and Oxone® (3 mmol) (previously mixed) was added during 30' (the reaction was exothermic). Stirring was continued for the appropriate time (see table). The reaction mixture was then filtered and the solvent was removed under vacuum. The crude was purified by crystallization or chromatography.