Ethylene carbonate → Methyl 4-(2-hydroxyethoxy)-3-(pyrrol-1-yl)benzoate

HRID 399834

Reaktionsgleichung

Reaktionsgleichung von HRID 399834
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.O=C1O[CH2:21][CH2:20][O:19]1>[I-].C([N+](CC)(CC)CC)C.C(OCC)(=O)C.O1CCCC1>[OH:19][CH2:20][CH2:21][O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1

Komponenten

6

Edukt 2

HCID 7303Ethylene carbonateHCID 18945287Methyl 4-hydroxy-3-(pyrrol-1-yl)benzoate

Produkt 1

HCID 18945225Methyl 4-(2-hydroxyethoxy)-3-(pyrrol-1-yl)benzoateAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6225Tetraethylammonium IodideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

The mixture of methyl 4-hydroxy-3-(pyrrol-1-yl)benzoate (1.5 g), 2-oxo-1,3-dioxolane (0.61 g) and tetraethylammonium iodide (0.38 g) was heated at 140° C. for 3 hours. The resultant mixture was dissolved in the solution of ethyl acetate and tetrahydrofuran. The solution was washed with water and dried over magnesium sulfate. Evaporation of the solvent gave the residue, which was purified by column chromatography on silica gel eluting with the solution of chloroform and ethyl acetate (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 4-(2-hydroxyethoxy)-3-(pyrrol-1-yl)benzoate (1.25 g) as an oil.

Aufarbeitung

  1. washThe solution was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent
  4. customgave the residue, which
  5. customwas purified by column chromatography on silica gel eluting with the solution of chloroform and ethyl acetate (9:1, V/V)
  6. additionThe eluted fractions containing the desired product
  7. customwere collected
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0565baedab7543e2b053a14ace790971
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05824691

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