N1CCOC[CH2:2]1.[CH:7](=O)[CH2:8][CH:9](C)C.S([O-])([O-])(=O)=O.[Mg+2].[CH3:19][C:20]1[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([CH3:31])O[C:22](=O)[CH:21]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:19][C:20]1[C:21]([CH:8]([CH3:9])[CH3:7])=[CH:22][CH:2]=[C:24]([CH3:31])[C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]
Morpholine (13.34 g), isovaleraldehyde (13.18 g), p-toluenesulfonic acid (0.2 g), and toluene (300 ml) were combined and heated at reflux using a Soxhlet extractor with magnesium sulfate to remove any water produced. After three hours the Soxhlet extractor was replaced with a condenser, and ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (30 g) was added. The reaction mixture was heated under reflux for approximately 64 hours. The solvent was evaporated, and the resultant oil was distilled to give 11.1 g of crude product which was chromatographed to yield ethyl 2,6-dimethyl-3-(1-methylethyl)benzoate (2.8 g).
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