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

HRID 551672노트

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HRID 551672 반응식
[CH2:1]([O:3][C:4]([O:6][Si](C)(C)C)=[CH2:5])[CH3:2].[CH3:11][O:12][C:13]1[CH:27]=[CH:26][C:16]([CH2:17][O:18][CH2:19][CH:20]([CH2:23][CH:24]=[CH2:25])[CH:21]=[O:22])=[CH:15][CH:14]=1>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>[OH:22][CH:21]([CH:20]([CH2:19][O:18][CH2:17][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:27][CH:26]=1)[CH2:23][CH:24]=[CH2:25])[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5]

참가 물질

5

반응물 2

HCID 98152811-Ethoxy-1-trimethylsiloxyetheneHCID 85824233HCID 85824233, 화합물

생성물 1

HCID 67198212HCID 67198212, 화합물

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매2회

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온도
-78 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-da3dab36d7114267b991f2301f5f9032
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947738B2

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