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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 10
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Original Articles

The Reaction of Enaminones with Grignard Reagents: Synthesis of α,β-Unsaturated Ketones

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Pages 1743-1753 | Received 08 Oct 1997, Published online: 20 Aug 2006

REFERENCES

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  • Patai , S. , Rappoport , Z. and Willey , J. , eds. 1989 . The Chemistry of Enones vols. 1 and 2 , Chichester
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  • Preparation of 3-(2,2-dimethyl ethoxy) propylmagnesium chloride 3b: A 250ml two-necked flask was charged with 4.84g (200mmol) of magnesium in 20ml of anhydrous THF under an argon flow. To initiate the reaction 0.2ml of 1,2-dibromoethane was added. When the solvent was refluxing, a solution of 10g (66mmol) of 3-(2,2-dimethyl ethoxy) propylchloride and 2ml of 1,2-dibromoethane in 100ml of anhydrous THF were added over 1h. After additional stirring under reflux for 2h, the solution was used immediately.
  • Brederek , H. , Effenberger , F. , Botsh , H. and Rehn , H. 1965 . Chem. Ber. , 98 : 1081
  • Bejan , E. , Aït-Haddou , H. , Daran , J. C. and Balavoine , G. G.A. 1996 . Synthesis , : 1012
  • The Enaminone 7 was obtained in 4 steps as shown in the Scheme 2. Scheme 2 For the first step see: Wohl R.A., Synthesis, 1974, 38. For the second step see: Frimer A.R., Synthesis, 1977, 578. For the oxidation step see: Mancuso A.J., Swern D., Synthesis, 1981, 165. For transformation of the monoprotected diketone to the corresponding enaminone 7 see ref. 9.

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