A Convenient Preparation of Iodoalkyl Esters from Lactones

References

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• Bromo and chloroalkyl esters usually were synthesized from lactones under harsh reaction conditions: HBr or HCI/ROH, reflux;J. Lavely and G. R. Proctor, Org. Syn., 45, 42 (1965); iodoalkyl esters required a multistep reaction sequence: Y. Knobler, S. Livergrand, and M. Frankel, J. Org. Chem., 24, 1794 (1959); C. Chang, K. K. Coward, J. Med. Chem., 19, 684 (1976); M. Frankel, Y. Knobler, J. Amer. Chem. Soc., 80, 3147 (1958); G. D. Johnson, W. B. Lindsey and B. R. Jones, J. Amer. Chem. Soc., 78, 461 (1956)
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• Chloroform could be employed also, carbon tetrachloride was not suitable due to phase-separation when the organosilicon reagent was added
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• in vacuo , 2 The reaction mixture was concentrated (40–50[ddot]/15 mm Hg). Carbon tetrachloride was added to the residue and the mixture concentrated again to give crude
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• Sieber , P. 1977 . Helv. Chim. Acta , 60 : 2711 H. Gerlach, Helv. Chim. Acta, 60, 3039 (1977)
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• Olah , G. A. , Narrang , S. C. , Salem , G. F. and Gupta , B. G. B. Synthesis , 1981 142 Since completion of this manuscript a iodotrimethylsilane-mediated transe sterification of esters under strictly neutral conditions with refluxing the reaction mixture overnight was described. These conditions apparently allow also the use of trimethylsilyl ethers instead of the alcohols for the trans esterification
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