Vinyl Acetate → 1-Methyl-4-vinyloxy-7-oxabicyclo[4.1.0]heptane

Participants

Reaction Steps

A mixture (100 mL) of sodium carbonate (0.06 mol) and toluene was heated to 95° C. 4.2 g of vinyl acetate was added dropwise to the mixture. Next, maintaining the temperature of the reaction mixture, and fifteen minutes later, further the mixture was combined with di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.5 mmol). Next, (6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)methanol (0.05 mol) was added dropwise over for two hours, and a reaction was carried out in a nitrogen atmosphere while adding dropwise 12.6 g of vinyl acetate and holding the reaction temperature at 95° C. After the completion of dropwise addition, the mixture was stirred for one hour. As the result of gas chromatography analysis of the mixture, it is confirmed that there was produced 1-methyl-4-vinyloxy-7-oxabicyclo[4.1.0]heptane represented by following Formula (14) in a yield of 95%. In 1H-NMR (CDCl3) analysis, signals specific to vinyl group were observed at 6.5 ppm, 4.2 ppm, and 4.05 ppm.

Provenance & Evidence