Devising a Synthesis Reaction Sequence

A multistep synthesis problem is shown below. Your challenge is to devise a series of reactions that will produce the desired product, from the designated starting compound. Choose a reagent from the list on the right to begin your synthesis sequence, and then press the Do Reaction button. The product (if any) from this reaction will appear in the window, accompanied by commentary in the information window just below it. You will then be promped to choose a reagent for the second step. In cases where your choice appears to be ineffective or unwise, you will be asked to press the Reset button and begin again.

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  (i) LiAlH4 in ether; (ii) H3O(+) workup
  Wolff-Kishner reaction (N2H4, heat with strong base)
  Jones' reagent (CrO3 in H3O(+) + acetone)
  CH3MgI (methylmagnesium iodide in ether or THF)
  conc. HBr (48%) & heat
  CH3SO2Cl (methanesulfonyl chloride & pyridine)
  CO2 (dry carbon dioxide gas), followed by H3O(+)
  5% H2SO4
  NaCN in aqueous acetone
  Mg metal turnings in ether
  HOCH2CH2OH (ethylene glycol), an acid catalyst and heat
  Wittig reagent ((C6H5)3P=CH2 in ether )

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This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to
JME Molecular Editor v2002.05 by: by Peter Ertl