MeO 22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an acetoacetic ester synthesis (Section 19.6). 5 3 6 CH₂O CI acetoacetic ester synthesis HC 7 MeO MeO 1 8 2-Methoxynaphthalene Nabumetone (a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at carbon 5 or 7. (b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum- etone is completed.
MeO 22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an acetoacetic ester synthesis (Section 19.6). 5 3 6 CH₂O CI acetoacetic ester synthesis HC 7 MeO MeO 1 8 2-Methoxynaphthalene Nabumetone (a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at carbon 5 or 7. (b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum- etone is completed.
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 63AP: As far back as the 16th century, South American Incas chewed the leaves of the coca bush,...
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