trimethyl(3-phenylprop-2-enyl)silane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). under cooling by ice the mixture was intensively stirred extracted by adding diethyl ether (10 mL) The reaction mixture was further extracted two times an organic layer was collected rinsed with a saturated aqueous sodium chloride solution (5 mL) by drying with anhydrous magnesium sulfate and concentration The residue was purified by thin layer chromatography (hexane/methylene chloride/diethyl ether=4/1/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). under cooling by ice the mixture was intensively stirred extracted by adding diethyl ether (10 mL) The reaction mixture was further extracted two times an organic layer was collected rinsed with a saturated aqueous sodium chloride solution (5 mL) by drying with anhydrous magnesium sulfate and concentration The residue was purified by thin layer chromatography (hexane/methylene chloride/diethyl ether=4/1/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an argon atmosphere, hafnium chloride (39.2 mg, 0.122 mmol) is suspended in anisole (3, 0.02 mL), and under ice cooling, an anisole (0.22 mL) solution of 4-(pivaloyloxy)benzaldehyde (1, 25 mg, 0.121 mmol) and trimethylcinnamylsilane (2, 46.7 mg, 0.245 mmol) was slowly added dropwise. After stirring overnight at room temperature, saturated sodium bicarbonate water (5 mL) was poured into the reaction mixture with vigorous stirring, diethyl ether (10 mL) was added and extraction was performed. Extractions were further carried out two times with diethyl ether (10 mL), the organic layers were combined, washed with a saturated sodium chloride aqueous solution (5 mL), dried with anhydrous magnesium sulfate, and concentrated. The residue was purified by thin layer chromatography (hexane:methylene chloride:diethyl ether=4:1:1), and the subject compound (4, 37.7 mg) was obtained as a colorless oily substance (yield 75%, syn/anti mixture). was added extraction Extractions washed with a saturated sodium chloride aqueous solution (5 mL) dried with anhydrous magnesium sulfate concentrated The residue was purified by thin layer chromatography (hexane:methylene chloride:diethyl ether=4:1:1) the subject compound (4, 37.7 mg) was obtained as a colorless oily substance (yield 75%, syn/anti mixture)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). under cooling by ice the mixture was intensively stirred extracted by adding diethyl ether (10 mL) The reaction mixture was further extracted two times an organic layer was collected rinsed with a saturated aqueous sodium chloride solution (5 mL) by drying with anhydrous magnesium sulfate and concentration The residue was purified by thin layer chromatography (hexane/methylene chloride/diethyl ether=4/1/1)