Vinyl Acetate → 1-Methyl-4-vinyloxy-7-oxabicyclo[4.1.0]heptane
Reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]([O:10][CH:11]=[CH2:12])(=O)[CH3:8].C[C:14]12[O:20][CH:19]1[CH2:18]C(CO)[CH2:16][CH2:15]2>C1(C)C=CC=CC=1>[CH3:12][C:11]12[O:10][CH:7]1[CH2:8][CH:14]([O:20][CH:19]=[CH2:18])[CH2:15][CH2:16]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- temperatureNext, maintaining the temperature of the reaction mixture, and fifteen minutes later
- customat 95° C
- additionAfter the completion of dropwise addition
- customAs the result of gas chromatography analysis of the mixture, it
Sources & evidence
- ORD record
- ord-459a97b66ad94170ad99076eb0d11928
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985866B2
Reaction notes
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