Scalable synthesis of dipyrromethanes

Details Scalable synthesis of dipyrromethanes Scalable synthesis of dipyrromethanes

2006-04-04

2006-04-04

Shameem, Golam M. M. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S400000, C548S517000

Reexamination Certificate

active

07022862

ABSTRACT:
A (preferably nonaqueous) method of making a dipyrromethane is described. The comprises the steps of: (a) providing a reaction system consisting essentially of an aldehyde or acetal, excess pyrrole and a catalyst; (b) reacting the aldehyde or acetal with the pyrrole in the reaction system to form the dipyrromethane therein; (c) quenching the reaction system by adding a base thereto (preferably without simultaneously or concurrently adding water and/or an organic solvent thereto); (d) separating the catalyst from the reaction system; and then (e) separating the pyrrole from the reaction system to produce the dipyrromethane as a residual

REFERENCES:
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U.S. Appl. No. 10/456,421, filed Jun. 6, 2003, Lindsey et al.
Hammel, Dirk, et al.,Synthesis and Reduction of 1,4-Phenylene-Bridged Oligoporphyrins, Advanced Materials, vol. 4, No. 11, pp. 737-739 (1992).
Littler, Benjamin J., et al.,Refined Synthesis of 5-Substituted Dipyrromethanes, The Journal of Organic Chemistry, vol. 64, No. 4, pp. 1391-1396 (1999).
Nagarkatti, Jia P., et al.,Synthesis of Pyridyl meso Substituted Dipyrrylmethenes, Synthesis, pp. 186-187 (Mar. 1974).
Staab, Heinz A., et al.,Synthesis and Properties of New Quinone-Bridged Diphenyl- and Tetraphenylporphyrins, Chem. Ber., vol. 127, pp. 223-229 (1994).
Vigmond, Stephen J., et al.,Direct Synthesis of Aryldipyrromethanes, Tetrahedron Letters, vol. 35, No. 16, pp. 2455-2458 (1994).

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