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Synthesis of 2-methoxy and 4-methoxy Equine Estrogens

Synthesis of 2-methoxy and 4-methoxy Equine Estrogens

P N Rao, C W Somawardhana

Steroids. Apr-May 1987;49(4-5):419-32.

PMID: 3455053

Abstract:

4-Methoxyequilin and 2-methoxyequilin were synthesized from the corresponding 4-bromoequilin and 2-iodoequilin derivatives, respectively, by nucleophilic displacement of halogen with methoxide ion in the presence of copper (II) chloride and 15-crown-5-ether. 4-Bromoequilin was prepared by reacting equilin with one equivalent of N-bromoacetamide. 2-Iodoequilin was prepared by reductive dehalogenation of 2,4-diiodoequilin, which in turn was obtained by treatment of equilin with two equivalents of iodine in methanolic ammonium hydroxide solution. 4-Methoxy-equilenin and 2-methoxyequilenin were prepared from the corresponding 4-iodo- and 2-iodo-7 epsilon, 8 epsilon-epoxyestrone derivatives, respectively. Nucleophilic displacement of iodine with methoxide ion was carried out as described earlier with simultaneous aromatization of the B ring leading to 4- and 2-methoxyequilenin derivatives. Alternatively, 4-methoxyequilenin was obtained from 4-methoxyequilin by selenium dioxide oxidation.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP517099	Equilenin solution		517-09-9	Price

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