Ethylene Oxide → 2-(3-Bromofuran-2-yl)ethan-1-ol

HRID 1778361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778361
C([Li])CCC.Br[C:7]1[O:8][CH:9]=[CH:10][C:11]=1[Br:12].[CH2:13]1[O:15][CH2:14]1.[Cl-].[NH4+]>C(OCC)C>[Br:12][C:11]1[CH:10]=[CH:9][O:8][C:7]=1[CH2:13][CH2:14][OH:15]

Komponenten

6

Edukt 4

HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 70215012,3-DibromofuranHCID 178418339Butyllithium

Produkt 1

HCID 639438362-(3-Bromofuran-2-yl)ethan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

n-Butyllithium (2.5M in hexanes, 12.9 mL) was added to a solution of 2,3-dibromofuran (6.63 g) in diethyl ether (40 mL) at −78° C. under nitrogen and the mixture was stirred for 15 minutes. A solution of ethylene oxide (15 mL) in diethyl ether (40 mL) was then added. The reaction mixture was stirred for a further 10 minutes then warmed to room temperature and stirred for 30 minutes. Saturated aqueous ammonium chloride was added and the organic layer was separated, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-25% to give 2-(3-bromofuran-2-yl)-ethanol (3.81 g) as a yellow oil.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for a further 10 minutes
  2. stirringstirred for 30 minutes
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-25%

Quellen und Nachweise

ORD-Eintrag
ord-e667d715e50049f897f234b06872a3b6
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266896B2

Notizen zur Reaktion

Wird geladen…