Isobutanol → Furmecyclox

Participants

Reaction Steps

A mixture of 85.2 parts of N-cyclohexyl-N-methoxyacetoacetamide and 58.2 parts of 95.7% pure α-acetoxypropionaldehyde is added dropwise to a suspension of 19.4 parts of iron-III chloride in 100 parts of isobutanol at 40°-45° C. The mixture is then kept at 45° C. for 7.5 hours. Water is added to the reaction mixture, the batch is extracted with methylene chloride and the extract is evaporated. 104 parts of crude product are obtained; this can be distilled at 138°-145° C./0.3 mm Hg, to give 88.5 parts of pure O-methyl-N-cyclohexyl-2,5-dimethylfuran-3-hydroxamic acid.

Provenance & Evidence