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

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.

SUBMITTER: Hylden AT

PROVIDER: S-EPMC3201045 | biostudies-other | 2011

REPOSITORIES: biostudies-other

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

Hylden Anne T AT Uzelac Eric J EJ Ostojic Zeljko Z Wu Ting-Ting TT Sacry Keely L KL Sacry Krista L KL Xi Lin L Jones T Nicholas TN

Beilstein journal of organic chemistry 20110923

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. ...[more]

PMID: 22043242

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