Ethanol → 2-(2-Hydroxyethyl)-4,5-dihydro-6,8-dimethylnaphtho[1,2-b]thiophene

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Reaction Steps

0.18 g of sodium boron hydride was added under nitrogen replacement and ice cooling to a 10 mL ethanol solution of 0.50 g of the compound obtained in Example 1, and the system was stirred for 2 hours at room temperature. After the reaction, reduced-pressure solvent distillation was performed, a saturated ammonium chloride aqueous solution was added under ice cooling, extraction was performed with ethyl acetate, and the organic layer was washed with saturated brine, dried with magnesium sulfate, and then subjected to reduced-pressure solvent distillation, and the residue was refined by silica gel column chromatography (25% ethyl acetate/hexane) to obtain 0.50 g of 2-(2-hydroxyethyl)-4,5-dihydro-6,8-dimethylnaphtho[1,2-b]thiophene (Table 9-1) in the form of a brown solid.

Provenance & Evidence