Dolbier HW Solutions 488

Dolbier HW Solutions 488 - C 6 H 5 CH(COOCH 2 CH 3 ) 2 C 6...

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21.11 The carbonyl oxygen at C-2 of pentobarbital is replaced by sulfur in Pentothal (thiopental). The sodium salt of Pentothal is formed by removal of a proton from one of the N @ H groups by sodium hydroxide. 21.12 The synthesis of phenobarbital requires diethyl 2-phenylmalonate as the starting material. Diethyl 2-phenylmalonate is prepared by a mixed Claisen condensation between ethyl phenyl- acetate and diethyl carbonate. 21.13 Like diethyl malonate, ethyl acetoacetate undergoes Michael addition to an a , b -unsaturated ketone. NaOCH 2 CH 3 CH 3 CH 2 OH 1 CH 3 CCH 2 COCH 2 CH 3 O O O CHCOCH 2 CH 3 CH 3 O C O O 1 NaOCH 2 CH 3 Ethyl phenylacetate C 6 H 5 CH 2 COCH 2 CH 3 O Diethyl carbonate CH 3 CH 2 OCOCH 2 CH 3 O Diethyl 2-phenylmalonate
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Unformatted text preview: C 6 H 5 CH(COOCH 2 CH 3 ) 2 C 6 H 5 CH(COOCH 2 CH 3 ) 2 Diethyl 2-phenylmalonate Phenobarbital C 6 H 5 CH 3 CH 2 O N N O O NaOCH 2 CH 3 CH 3 CH 2 Br Diethyl 2-ethyl-2-phenylmalonate C 6 H 5 C(COOCH 2 CH 3 ) 2 CH 2 CH 3 H 2 NCNH 2 O H H Pentothal sodium CH 3 CH 2 CH 2 CH CH 3 CH 2 O N N O S CH 3 Na 1 2 CH 3 CH 2 CH 2 CH CH 3 CH 2 O N N O S 2 CH 3 Na 1 H H Pentobarbital; prepared from urea, (H 2 N) 2 C O CH 3 CH 2 CH 2 CH CH 3 CH 2 O N N H H O O CH 3 1 3 4 6 2 5 Pentothal; prepared from thiourea, (H 2 N) 2 C S CH 3 CH 2 CH 2 CH CH 3 CH 2 O N N H H O S CH 3 582 ESTER ENOLATES...
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