310-23 - Organic Lecture Series CH 310 N LECTURE 23...

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Organic Lecture Series 1 CH 310 N LECTURE 23 Textbook Assignment: Chap 19 Cont’d Homework (for credit): POW 7 posted (Due Mar 21) Today’s Topics: Enamines & Enolates in synthesis Notice & Announcements: “Window into the Soul” Brian Berger, M.D. - Ophthalmology Organic Lecture Series 2 Enolate Enolate Anions Anions and and Enamines Enamines Chapter 19
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Organic Lecture Series 3 –the ester with no α -hydrogens is generally used in excess Ph OCH 3 O 3 O 1. CH 3 O - Na + 2. H 2 O, HCl 3 OO Methyl propanoate benzoate + Methyl 2-methyl-3-oxo- 3-phenylpropanoate (racemic) Crossed Crossed Claisen Claisen Condensations Condensations Only this enolate can be formed Organic Lecture Series 4 Claisen Claisen condensations as routes to condensations as routes to ketones ketones OEt O O O 1. EtO + 2 3. NaOH, H 2 O, heat O O 4. H 2 5. heat O OH CO 2 O O Et OH + + Reactions 1 & 2: Claisen condensation followed by acidification Reactions 3 & 4: Saponification and acidification Reaction 5: thermal decarboxylation + This segment was added
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Organic Lecture Series 5 The result of Claisen condensation, saponification, acidification, and decarboxylation is a ketone: R- CH 2 -C OR' O R O CH 2 -C-OR' 2 -C- 2 -R O 2HOR ' CO 2 + + several steps + from the ester furnishing the enolate anion furnishing the carbonyl group Claisen Claisen condensations as routes to condensations as routes to ketones ketones Organic Lecture Series 6 Enamines are formed by the reaction of a amine with the carbonyl group of an aldehyde or ketone the 2° amines most commonly used to prepare
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310-23 - Organic Lecture Series CH 310 N LECTURE 23...

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