Friday_Session_5_solution

Friday_Session_5_solution - Chem 3580 Spring 2009 Friday...

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Chem 3580 - Spring 2009 Friday Session 5 - Solutions 1. Design a laboratory multistep synthesis for each of the following compounds from the indicated starting materials as the only sources of carbon . You may use any inorganic reagents and/or other organic reagents so long as they don’t supply any carbon to the final product. (a) OH CH 3 O Cl Cl O HO HO O OH O (CH 3 ) 2 CuLI OH O 1. LiAlH 4 2. H 3 O + OH PCl 3 Cl Mg, ether MgCl OH O SOCl 2 Cl O (CH 3 ) 2 CuLI O MgCl 2. H 3 O + 1. OH CH 3 (b) OH OCH 3 O O Ph 3 P O CH 3 O O CH 3 O H O CH 3 O 1. HAl(iBu) 2 2. H 3 O + O Ph 3 P O CH 3 O OCH 3 O OH 1. LiAlH 4 2. H 3 O + H (c) OH O BrMg + Br HO O MgBr Br Alternative Forward synthesis for top scheme only. You should do the alternative one on your own. 1. NaBH 4 2. H 2 O HO PBr 3 Br O Mg, ether BrMg O 1. 2. H 2 O OH H 2 SO 4 H 2 , Pd/C
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(d) O Br O H OH + Ph 3 P CH 2 CH 3 Br OH O H 1. LiAlH 4 2. H 3 O + OH PBr 3 Br 1. Mg, ether 2. H 2 O + MgBr O H MgBr 1. 2. H 3 O + CrO 3 , pyridine CH 3 Br 1. PPh 3 2. n-BuLi Ph 3 P CH 2 Ph 3 P CH 2 (or MnO 2 , PCC) OH O Ylide synthesis
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell.

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Friday_Session_5_solution - Chem 3580 Spring 2009 Friday...

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