1559T_ch20_358-37210/18/054:24Page369 ⊕ EQA Soufionso Problems369 56.Baeyer-Villiger reaction.followed by ester hydrolysis 13 C=0 57.Several ways will work.One that uses a reaction from this chapter (the actual route used)is shown below C)TFproduct CH; (Wug） CO,H ⊕ 58.1.(CH3)2NH.A(makes N.N-dimethyl carboxamide),2.LiAH.(CHCH)O(makes amine).3.H 59.Pay attention to the stereochemistry. 》-so,a,Pyridine 2.KCN.DMSC OH C电=product Wittig reaction CHa 56. Baeyer-Villiger reaction, followed by ester hydrolysis. 57. Several ways will work. One that uses a reaction from this chapter (the actual route used) is shown below. 58. 1. (CH3)2NH, (makes N,N-dimethyl carboxamide), 2. LiAlH4, (CH3CH2)2O (makes amine), 3. H, H2O 59. Pay attention to the stereochemistry. CH3 O product Deprotonation at
-carbon allows isomerization to more stable equatorial stereoisomer CH2 P(C6H5)3, THF Wittig reaction CH3 etc. CN 2. H, H2O 1. CH3Li, THF Makes methyl ketone KOH, CH3OH CH3 O CH3 etc. CH3 etc. CH3 OH etc. SO2Cl, pyridine 2. KCN, DMSO 1. CH3 CH3 product CH3 CH O (Wittig) (C6H5)3P C(CH3)2, THF 2. HAl[CH2CH(CH3)2]2, toluene, 60 1. H, CH3OH (makes ester) CH3 CH3 CO2H MCPBA CH2Cl2 KOH, H2O, H O H OH CH3 H O C O CH3 Solutions to Problems • 369 1559T_ch20_358-372 10/18/05 4:24 Page 369