Ammonium Chloride → 7-Methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-3,4-dihydronaphthalene

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Reaction Steps

2-iodo-7-methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-1,2,3,4-tetrahydronaphthalene (5, 39.4 mg, 0.0729 mmol) was dissolved in toluene (1.5 mL), and 1,8-diaza-bicyclo[5.4.0]undecene-7 (DBU, 0.035 mL, 0.234 mmol) was added, with heating and stirring at 80° c. for 15 min. After standing to cool, a saturated ammonium chloride aqueous solution (10 mL) was added under ice cooling, vigorously stirred, and next, extraction was carried out adding diethyl ether (10 mL). Extractions were further carried out two times with diethyl ether (10 mL), the organic phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated. The residue was purified by thin layer chromatography (benzene:hexane=10:1), and the subject compound (6, 22.7 mg) was obtained as a colorless oily substance (yield=75%).

Provenance & Evidence