Triethylamine → Bis-[(2-triethylsilyl-4-furyl)methyl]oxalate

HRID 1109891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1109891
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[OH:7][CH2:8][C:9]1[CH:10]=[C:11]([Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[O:12][CH:13]=1.C(N([CH2:26][CH3:27])CC)C>ClCCl>[CH2:15]([Si:14]([CH2:17][CH3:18])([CH2:19][CH3:20])[C:11]1[O:12][CH:13]=[C:9]([CH2:8][O:7][C:1](=[O:5])[C:2]([O:7][CH2:8][C:9]2[CH:10]=[C:11]([Si:14]([CH2:26][CH3:27])([CH2:17][CH3:18])[CH2:15][CH3:16])[O:12][CH:13]=2)=[O:3])[CH:10]=1)[CH3:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 150370354-Hydroxymethyl-2-triethylsilylfuran2×

Produkt 1

HCID 15037121Bis-[(2-triethylsilyl-4-furyl)methyl]oxalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Oxalyl chloride (0.59 ml, 6.79 mmol) was added dropwise to a solution of 4-hydroxymethyl-2-triethylsilylfuran (Compound 1, 1.2 g, 5.66 mmol) and triethylamine (0.95 ml, 6.79 mmol) in dichloromethane (10 ml) at 0°. After 10 minutes, the reaction mixture was quenched with ice. Extraction (dichloromethane) and evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromotograhy on silica using 5% ethyl ether/hexane. Fractions with Rf of about 0.17 gave, after evaporation the title oxalate ester as a colorless oil.

Aufarbeitung

  1. customthe reaction mixture was quenched with ice
  2. extractionExtraction (dichloromethane) and evaporation of the
  3. dry with materialdried (magnesium sulfate)
  4. customextracts gave an oil, which
  5. customwas purified by flash chromotograhy on silica using 5% ethyl ether/hexane
  6. customFractions with Rf of about 0.17 gave
  7. customafter evaporation the title oxalate ester as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-9b63b808f0ca44ccbdccd41d684fe43f
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05322953

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