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11. 4-Bromo-3-[(trimethylsilyl)methyl]-1,2-butadiene was prepared from 2-butyn-1,4-diol as in the following scheme.
12. To a solution of indium [indium powder (99.99%) purchased from Aldrich Chem. Co.; 58 mg, 0.5 mmol) in DMF
(0.6 mL) was added 4-bromo-3-[(trimethylsilyl)methyl]-1,2-butadiene (110 mg, 0.5 mmol) in DMF (0.6 mL). After
the reaction mixture was stirred for 30 min at room temperature, benzaldehyde (37 mg, 0.35 mmol) was added.
After 40 min at room temperature, the reaction mixture was quenched with saturated aqueous NaHCO3 solution.
The aqueous layer was extracted with ether (3×25 mL), and the combined organic layers were washed with water
(20 mL), brine (20 mL), dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by silica
gel chromatography (hexane:EtOAc=20:1) leading to 1-phenyl-3-trimethylsilylmethyl-3,4-pentadien-l-ol (80 mg,
92%).
1
13. All new compounds have satisfactory analytical data including H, 13C NMR, MS and IR spectroscopy.
.