Methyl morpholine oxide → (2-Benzyloxy-6-methoxyphenyl)-(4-methoxyphenyl)methanol

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Reaction Steps

In a nitrogen stream, a solution of (2-benzyloxy-6-methoxyphenyl)-methanol (3.52 g, 14.41 mmol) and N-methylmorpholine N-oxide (NMO, 2.53 g, 21.61 mmol) in dichloromethane (14.5 mL) was cooled in a water bath, and tetra-n-propylammonium perruthenate (TPAP, 152 mg, 0.43 mmol) was added thereto. The reaction mixture was stirred for 20 minutes at the same temperature and at room temperature for 1.75 hours, and then subjected to Celite filtration and the solvent was distilled under reduced pressure. The obtained residue was treated by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:3 to 1:2.5)]. The obtained compound was dissolved in THF and cooled in a water bath, and a solution of 4-methoxyphenylmagnesium bromide in THF (0.5 M, 30.3 mL) was added dropwise thereto in a nitrogen stream. The reaction mixture was stirred at room temperature for 1.25 hours, and then a saturated ammonium chloride aqueous solution was added thereto at room temperature and the mixture was extracted with ether. The organic layer was washed with a saturated ammonium chloride aqueous solution and dried (anhydrous sodium sulfate), and then the solvent was distilled under reduce pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:4 to 1:3.5)] to obtain the title compound (3.66 g, 72%).

Provenance & Evidence