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

Temperature

-78 °C

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%).

1. stirringthe mixture was stirred at this temperature for 1.5 hours
2. customThe reaction was terminated by the addition of a saturated aqueous solution of sodium bicarbonate (100 mL) and water (100 mL)
3. extractionfollowed by extraction with methylene chloride
4. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water, and saturated saline
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationThe residue was filtered
7. concentrationconcentrated under reduced pressure
8. customThen, the obtained crude product
9. customwas purified by silica gel column chromatography
10. customto obtain the compound of interest as an oil substance (1.31 g, 48%)

ORD record

ord-da3dab36d7114267b991f2301f5f9032

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2