FR_session_7 - O OEt This is Darzens condensation reaction...

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Chem 3580 – Spring 2009 Friday Session 7 1. Provide the forward synthesis for each retrosynthetic analysis. O OH O O O OH O O O H O O O OEt O OH O OEt Warfarin (racemic) anticoagulant (blood thinner) + + (a) NH 2 COOH NH 2 COOEt CN COOH COOEt COOEt O COOEt COOEt Gabapentin (b) N O O Ph Phensuximide OEt OEt O O Ph OH OH O O Ph Ph H OEt O OEt O O NC OEt O Ph OEt O OH O Ph OH O OH O (c) 2. Provide a laboratory synthesis for the following compounds from the indicated starting materials O H H from EtO OEt O O Br Br (a) N CO 2 Me MeO 2 C H NO 2 from H O MeO OMe O O NH 3 Nifedipine (Procardia) (b) NO 2 3. Suggest a plausible mechanism for each of the following reactions. H O H OH 1. CH 3 COO Na + 2. H 2 O, HCl O H O + O O O (a) H O + Br OEt O t-BuOK t-BuOH O
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Unformatted text preview: O OEt This is Darzens condensation reaction OEt OEt O O + O 1. NaOEt, EtOH 2. H 3 O + O O EtO 2 C CO 2 Et (b) Ph Ph O O I 2 (exs) HO PhCOO + HCI 3 (yellow precipitate) (c) Ph H O 1. EtO (1 equiv), EtOH 2. KCN, EtOH 3. H 3 O + , ! Ph CO 2 H CO 2 H + NC CO 2 Et (d) OEt OEt O O 1. EtO , EtOH 2. H 3 O + , ! O O From Problem Set 8 (e) 4. Selected Problems from Problem Set 9 from O O O from O from O Only source of carbon O H EtONa, EtOH H OEt O (exs) A O t-BuOK B KOH, H 2 O O H...
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This note was uploaded on 10/25/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell University (Engineering School).

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FR_session_7 - O OEt This is Darzens condensation reaction...

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