Chapter 19: Problem 42
2 The following intermediate was needed for the synthesis of tamoxifen, a widely used antiestrogen drug for treating estrogen-dependent cancers such as breast and ovarian cancer.
Chapter 19: Problem 42
2 The following intermediate was needed for the synthesis of tamoxifen, a widely used antiestrogen drug for treating estrogen-dependent cancers such as breast and ovarian cancer.
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Get started for freeEnamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of \(C\)-alkylation and \(N\)-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.
Show how to use alkylation or acylation of an enamine to convert acetophenone
to the following compounds.
(a)
Show how the sequence of Michael reaction, hydrolysis, acidification, and thermal decarboxylation can be used to prepare pentanedioic acid (glutaric acid).
Show how the tranquilizer valnoctamide can be synthesized using diethyl malonate as the source of the carboxamide group.
Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin \(A\). (a) Addition of one mole of \(\mathrm{HCl}\) to isoprene gives 4 -chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity. (b) Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate.
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