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Over all Goals

Intramolecular and Intermolecular  Cyclopropanation Studies using Ethyl 2-diazo-3-oxooct-7-enoate and Cyclohexene. Over all Goals. Synthesis Ethyl 3-oxooct-7-enoate Purified the compound Carry out diazo transfer reaction

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Over all Goals

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  1. Intramolecular and Intermolecular Cyclopropanation Studies usingEthyl 2-diazo-3-oxooct-7-enoateand Cyclohexene

  2. Over all Goals • Synthesis Ethyl 3-oxooct-7-enoate • Purified the compound • Carry out diazo transfer reaction • Begin the intermolecular and intramolecular cyclopropanation reaction competitions • Determine which products are minors and which are majors. • Collect Data • Rest…..

  3. Original Compound • Ethyl 3-oxooct-7-enoate • Molecular weight of 184.26 grams • Appearance characterized by a golden yellow color

  4. Synthesis of Enolate Compound • The reaction is ran in a nitrogen atmosphere.

  5. The Work Begin • The first part of the reaction is between Lithium Diisopropylamide (LDA) and ethyl acetoacetate. • The product is a dienolate.

  6. The Work Continue • The second step is the reaction between the dienolate and 3-bromobut-1-ene (alkyl halide). • The product is Ethyl 3-oxooct-7-enoate

  7. Synthesis Apparatus

  8. Did the proposed synthesis work? • TLC • 3 part methylene chloride and two part methanol • 3 part ligroin and 1 part ethyl acetate • A sample is analyzed using a Gas Chromatography -Mass Spectrophotometer, also known as GC-MS.

  9. GC-Mass Specs

  10. Purification • Column Chromatography • Solvent • 3 part Hexane to 1 part ethyl acetate • Purified the crude solution • 3 part ligroin and 1 part ethyl acetate • Vacuum distillation in hot oil bath

  11. Alternative routeSynthesis of ethyl 3-oxohept-6-enoate • The process is similar to a Grignard Reaction. • Everything was done in one flask.

  12. Proposed Mechanism 2 2 2

  13. GC-MS of Grignard

  14. Diazo-transfer • Once the enolate compound is made, the next step is a Dizao transfer.

  15. First step of Diazo transfer • The first part of the reaction is between tosyl chloride and sodium azid. • The product that was made from this reaction was tosyl azid and table salt (NaCl).

  16. Second steps of Diazo Transfer • React the tosyl azid with the enolate compound in diethyamide and diethyl ether to get a diazo compound.

  17. Cyclopropanation reaction • In theory

  18. Usage of cyclopropanation

  19. Acknowledgement • Department of natural science for funding • Dr. Hornbuckle for the guidance • Joe Holak (research partner) • Matthew Shellnutt (research partner)

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