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

Participants

Reaction Conditions

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), then 1,8-diazabicyclo[5.4.0]undecene-7 (DBU, 0.035 mL, 0.234 mmol) was added thereto, and the mixture was stirred for 15 minutes while heating at 80° C. After allowing cooling, a saturated aqueous ammonium chloride solution (10 mL) was added under cooling by ice, and then the mixture was intensively stirred and extracted by adding ether (10 mL). The reaction mixture was further extracted two times using ether (10 mL), and then an organic layer was collected and rinsed with a saturated aqueous sodium chloride solution, followed by drying with anhydrous magnesium sulfate and concentration thereof. The residue was purified by thin layer chromatography (benzene/hexane=10/1) to obtain the title compound (6, 22.7 mg) as a colorless oily substance (yield 75%).

Provenance & Evidence