Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

AT Hylden, EJ Uzelac, Z Ostojic, TT Wu…

Index: Hylden, Anne T.; Uzelac, Eric J.; Ostojic, Zeljko; Wu, Ting-Ting; Sacry, Keely L.; Sacry, Krista L.; Xi, Lin; Jones, T. Nicholas Beilstein Journal of Organic Chemistry, 2011 , vol. 7, p. 1323 - 1326

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Citation Number: 2

Abstract

Abstract The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2-cyclohexenones proceeds in good yields (58–90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium (III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy- 2-cyclohexenones.