Sodium hydride → 3-Ethoxy-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenone

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Reaction Steps

A suspension of 3-ethoxy-5-(2-hydroxyphenyl)-2-cyclohexenone (32.4 g) in tetrahydrofuran (400 ml) was added slowly to an ice-cooled suspension of sodium hydride (3.34 g) in tetrahydrofuran (75 ml). The mixture was stirred at room temperature for 30 min, cooled in an ice-bath and a solution of methoxyethoxymethyl chloride (20.8 g) in tetrahydrofuran (50 ml) was added dropwise with stirring. The mixture was stirred overnight at room temperature and then was concentrated by the removal of most of the tetrahydrofuran under reduced pressure. The concentrate was diluted with water and extracted with ether. The ethereal extracts were dried and the solvent removed under reduced pressure. The residual oil was purified by column chromatography on silica gel using chloroform for elution to afford the title compound (36.23 g) as a pale yellow oil.

Provenance & Evidence