1-Ethoxy-1-trimethylsiloxyethene → HCID 67198212, compound

Participants

Reaction Conditions

Reaction Steps

A methylene chloride solution (10 mL) of titanium tetrachloride (0.97 mL, 8.88 mmol) and [(1-ethoxyvinyl)oxy](trimethyl)silane (J. Am. Chem. Soc. 2003, 125, 5644) was added to a methylene chloride solution (80 mL) of 2-{[(4-methoxybenzyl)oxy]methyl}pent-4-enal (Tetrahedron: Asymmetry 2001, 12, 3223) (1.98 g, 8.46 mmol) with stirring at −78° C., and the mixture was stirred at this temperature for 1.5 hours. The reaction was terminated by the addition of a saturated aqueous solution of sodium bicarbonate (100 mL) and water (100 mL), followed by extraction with methylene chloride. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water, and saturated saline and dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (1.31 g, 48%).

Provenance & Evidence