By Elimination of Functionality from Substituted-Alkyl Substituents

By Elimination of Functionality from Substituted-Alkyl Substituents 

Alkyl substituents that bear a functional group may be converted into simple unsubstituted alkyl groups in several ways, as illustrated briefly in the following examples. The reverse processes are covered in Section 2.2.4. 

2-(3-Hydroxy-3-methylbut-l-ynyl)quinoxaline (113) gave 2-ethynylquinoxaline (114) by loss of acetone (dry NaOH, PhMe, reflux, 2 h 75%) 842 several analogs were made similarly.569,842 

3-Carboxymethyl- (117, R = C02H) gave 3-methyl-2( 1 //)-quinoxalinone (117, R = H) by decarboxylation (neat, 190°C, sublimation tube, 2h 50%).81 

3-Etboxalylmethyl-l-methy]-2( 1 //)-quinoxalinone (118) underwent deacylation to give 1,3-dimethyl-2(l//)-quinoxalinone (119) (80% H2NNH2H2O, reflux, 

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