Water → 3-(5-Methoxymethyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde

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Reaction Conditions

Reaction Steps

To a cold solution (0° C.) of sodium hydride in tetrahydrofuran (4 mL), under an atmosphere of argon, was added 3-(5-hydroxymethyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde (example 10c) (246 mg, 0.67 mmol) in tetrahydrofuran (6 mL). The mixture was stirred at 0° C. for 15 minutes, then the argon flow was stopped and methyl iodide was added. After 3 hours at room temperature, the mixture was diluted with ethyl acetate. Water was slowly added and the layers separated. The organic layer was further washed with water, brine, dried (MgSO4), filtered and evaporated. The residue was chromatographed on silica gel (20% ethyl acetate in hexane) to afford 99 mg of 3-(5-Methoxymethyl-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde. 39% yield. 1H-NMR (300 MHz, CDCl3): 1.39 (s, 6H), 2.11 (s, 3H), 4.27 (s, 2H), 5.09 (s, 2H), 7.17 (s, 2H), 7.49 (d, J=8.5 Hz, 1H), 7.93 (dd, J1=8.5 Hz, J2=2.1 Hz, 1H), 8.02 (d, J=2.1 Hz, 1H), 10.03 (s, 1H).

Provenance & Evidence