15597.eh23.409-42210/21/0523:33Page414 EQA 414.Chapter 23 ESTER ENOLATES AND THE CLAISEN CONDENSATON CH Br (d)1.2 NaOCH2CH3.2. ,3.NaOH.H,0,4.H,H,0.4 人CH,B 30.a +CH=CHCCH, →product CH.CHOH b NaOCH.CH CO2CH-CH 31.Here is one way that gets the job done 32.(a)R (b)H2N (c),(d)Does not work:An O-H bond is necessary (see the mechanisms above).(d) 1. 2 NaOCH2CH3, 2. , 3. NaOH, H2O, 4. H
, H2O, 30. (a) (b) (c) 31. Here is one way that gets the job done: 32. (a) (b) (c), (d) Does not work: An OOH bond is necessary (see the mechanisms above). O O C H O H H O O C H2N H2N H O H H O O O R C H O H H O O C O R H O H H O O O H C H O H H O O C O H H O H H Cat. NaOCH2CH3 CH3CH2OH (Michael addition) 1. NaOH, H2O 2. H
, H2O, CO2 O O O O
CH product 3CCH2CO2CH2CH3 CO2CH2CH3 Cat. NaOCH2CH3 CH3CH2OH
CH2(CO2CH2CH3)2 product O Cat. NaOCH2CH3 CH3CH2OH (Michael addition) CH2 CHCCH3 O O
product O CH2Br , CH2Br 414 • Chapter 23 ESTER ENOLATES AND THE CLAISEN CONDENSATION 1559T_ch23_409-422 10/21/05 23:33 Page 414