Treatment of ketone A with LDA followed by CH3CH2I did not form the desired alkylation

Chapter 23, Problem 23.69

(choose chapter or problem)

Treatment of ketone A with LDA followed by CH3CH2I did not form the desired alkylation product B. What product was formed instead? Devise a multistep method to convert A to B, a synthetic intermediate used to prepare the anticancer drug tamoxifen (Section 23.8C and the chapter-opening molecule). HO O A HO B O

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