Dolbier HW Solutions 487

Dolbier HW Solutions 487 - 581 ESTER ENOLATES 21.9...

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21.9 Alkylation of ethyl acetoacetate with 1,4-dibromobutane gives a product that can cyclize to a f ve- membered ring. Saponi f cation followed by decarboxylation gives cyclopentyl methyl ketone. 21.10 The last step in the synthesis of pentobarbital is the reaction of the appropriately substituted deriva- tive of diethyl malonate with urea. The dialkyl derivative of diethyl malonate is made in the usual way. It does not matter whether the ethyl group or the 1-methylbutyl group is introduced f rst. CH 2 (COOCH 2 CH 3 ) 2 Diethyl malonate CH 3 CH 2 CH 2 CH CH 3 CH 3 CH 2 C(COOCH 2 CH 3 ) 2 Diethyl 2-ethyl-2-(1-methylbutyl)malonate 2. NaOCH 2 CH 3 , CH 3 CH 2 Br 1. NaOCH 2 CH 3 , CH 3 CH 2 CH 2 CHCH 3 Br 1 COCH 2 CH 3 COCH 2 CH 3
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