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Synthesis and dehydration reaction of 1-(4-benzyloxyphenyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphth-2-ol: possible intermediate of Lasofoxifene
Authors: Hejtmánková Ludmila | Jirman Josef | Sedlák Miloš
Year: 2009
Type of publication: článek v odborném periodiku
Name of source: Research on Chemical Intermediates
Publisher name: Springer
Place: Dordrecht
Page from-to: 615-623
Titles:
Language Name Abstract Keywords
cze Syntéza a dehydratace 1-(4-benzyloxyfenyl)-6-methoxy-2-fenyl-1,2,3,4-tetrahydronaft-2-ol: možného intermediátu Lasofoxifenu Článek se zabývá syntézou klíčového prekurzoru Lasofoxifenu. 1-(4-Benzyloxyfenyl)-6-methoxy-2-fenyl-3,4-dihydronaftalen byl připraven sekvencí pěti reakčních kroků: v prvním byl ve výtěžku 70% připraven 1-(4-benzyloxyfenyl)-6-methoxy-3,4-dihydronaftalen, který byl kvantitativně epoxidován na 7b-[4-(benzyloxy)fenyl]-5-methoxy-1a,2,3,7b-tetrahydronafto[1,2-b]oxiren. Katalytická (ZnI2) isomerizace epoxidu poskytla 1-(4-benzyloxyfenyl)-6-methoxy-1,2,3,4-tetrahydronaftalen-2-on (75%). Jeho následná reakce s fenylmagnesium bromidem poskytla 1-(4-benzyloxyfenyl)-6-methoxy-2-fenyl-1,2,3,4-tetrahydro-2-naftol (87%). Kysele katalyzovaná dehydratace tototo alkoholu působením polyfosforečné kyseliny (25 °C) vede k 1-(4-benzyloxyfenyl)-6-methoxy-2-fenyl-1,4-dihydronaftalenu (80%). Dehydratace v systému acetanhydrid/polyfosforečná kyselina poskytuje 1-(4-benzyloxyfenyl)-6-methoxy-2-fenyl-3,4-dihydronaftalen (66%). Grignardova reakce; Epoxidace; Olefinace; Regioselektivita; Dihydronaftaleny
eng Synthesis and dehydration reaction of 1-(4-benzyloxyphenyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphth-2-ol: possible intermediate of Lasofoxifene The paper deals with a simple and sufficient synthesis of key precursor of Lasofoxifene. The 1-(4-benzyloxyphenyl)-6-methoxy-2-phenyl-3,4-dihydronaphthalene was prepared by a sequence of five reactions steps: first 1-(4-benzyloxyphenyl)-6-methoxy-3,4-dihydronaphthalene was prepared (70%), and this was quantitatively epoxidized to 7b-[4-(benzyloxy)phenyl]-5-methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene. Catalytic (ZnI2) isomerization of the epoxide gave 1-(4-benzyloxyphenyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-one (75%). Its subsequent reaction with phenylmagnesium bromide gave 1-(4-benzyloxyphenyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydro-2-naphthol (87%). Acid-catalysed dehydration of this alcohol by polyphosphoric acid (25A degrees C) provides 1-(4-benzyloxyphenyl)-6-methoxy-2-phenyl-1,4-dihydronaphthalene (80%). Dehydration in the system of acetic anhydride/polyphosphoric acid gives 1-(4-benzyloxyphenyl)-6-methoxy-2-phenyl-3,4-dihydronaphthalene (66%). Grignard reaction; Epoxidation; Olefination; Regioselectivity; Dihydronaphthalenes

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