Anisole → 1-(4-Methoxyphenyl)-2-phenyl-1-(4-pivaloyloxyphenyl)-3-butene

Hafnium chloride (39.2 mg, 0.122 mmol) was suspended in anisole (3, 0.02 mL) under an argon atmosphere, and then an anisole solution (0.22 mL) of 4-(pivaloyloxy)benzaldehyde (1, 25 mg, 0.121 mmol) and trimethyl cinnamylsilane (2, 46.7 mg, 0.245 mmol) was slowly added dropwise thereto under cooling by ice. The reaction mixture was stirred overnight at room temperature, then a saturated aqueous sodium bicarbonate solution (5 mL) was poured thereto, and the mixture was intensively stirred and extracted by adding diethyl ether (10 mL). The reaction mixture was further extracted two times using diethyl ether (10 mL), and then an organic layer was collected and rinsed with a saturated aqueous sodium chloride solution (5 mL), followed by drying with anhydrous magnesium sulfate and concentration thereof. The residue was purified by thin layer chromatography (hexane/methylene chloride/diethyl ether=4/1/1) to obtain the title compound as a colorless oily substance (37.7 mg, yield 75%, cin/anti mixture).

1. temperatureunder cooling by ice
2. stirringthe mixture was intensively stirred
3. extractionextracted
4. additionby adding diethyl ether (10 mL)
5. extractionThe reaction mixture was further extracted two times
6. customan organic layer was collected
7. washrinsed with a saturated aqueous sodium chloride solution (5 mL)
8. dry with materialby drying with anhydrous magnesium sulfate and concentration
9. customThe residue was purified by thin layer chromatography (hexane/methylene chloride/diethyl ether=4/1/1)

ORD record

ord-c5aefdce3aa74c64aa175a4a06793f4d

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193394B2