Ethylene Oxide → 2-Ethyl-5-(2-hydroxyethyl)furan

HRID 1061477

Reaktionsgleichung

Reaktionsgleichung von HRID 1061477
[Li]CCCC.[CH2:6]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)[CH3:7].[CH2:13]1[O:15][CH2:14]1.[NH4+].[Cl-]>C1COCC1>[CH2:6]([C:8]1[O:9][C:10]([CH2:13][CH2:14][OH:15])=[CH:11][CH:12]=1)[CH3:7]

Komponenten

6

Edukt 4

HCID 6354Ethylene OxideHCID 185542-EthylfuranHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Produkt 1

HCID 218749232-Ethyl-5-(2-hydroxyethyl)furanAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

n-BuLi (2.5 M in hexane, 4.4 mL, 11 mmol) was added to a solution of 2-ethylfuran (1.05 mL, 10 mmol) in THF (10 mL) at −25° C. The solution was warmed to rt and stirred for 3 h. Ethylene oxide (0.75 mL) was added at −78° C. The reaction was stirred for 0.5 h at −15° C. and overnight at rt. Aqueous sat. NH4Cl was added and the mixture was extracted with ether (3×). The combined extracts were washed with water (1×) and brine (1×) and dried over Na2SO4. Purification by flash chromatography on silica gel eluting with 30% EtOAc/70% hexane gave 1.12 g (8.02 mmol, 80.2%) of 2v(1) as a yellow oil.

Aufarbeitung

  1. stirringThe reaction was stirred for 0.5 h at −15° C. and overnight at rt
  2. extractionthe mixture was extracted with ether (3×)
  3. washThe combined extracts were washed with water (1×) and brine (1×)
  4. dry with materialdried over Na2SO4
  5. customPurification by flash chromatography on silica gel eluting with 30% EtOAc/70% hexane

Quellen und Nachweise

ORD-Eintrag
ord-15dc23341d5442599ff6ffff220b6f22
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960474B2

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