Triethylamine → 6-Fluoro-3-methyl-1,2-benzoxazole

HRID 277361

Reaktionsgleichung

Reaktionsgleichung von HRID 277361
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[C:4]([OH:11])[CH:3]=1.C(N1C=CN=C1)([N:14]1C=CN=C1)=O.C(N(CC)CC)C>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]([CH3:9])=[N:14][O:11][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27373264'-Fluoro-2'-hydroxyacetophenone

Produkt 1

HCID 219784096-Fluoro-3-methyl-1,2-benzoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 4′-fluoro-2′-hydroxyacetophenone, oxime (47.0 g, 0.278 mol) in tetrahydrofuran is heated to just under reflux, treated with a solution of 1,1′-carbonyldiimidazole (55.0 g, 0.340 mol) and triethylamine (39.0 g, 0.390 mol) in tetrahydrofuran, refluxed for one hour, cooled, concentrated in vacuo, and poured into an ice-water mixture. The resultant aqueous mixture is extracted with ether. The organic extracts are combined, washed sequentially with saturated ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and a methylene chloride/hexanes solution (1:1) gives the title product as a yellow oil which is identified by 1H NMR spectral analysis.

Aufarbeitung

  1. temperatureis heated to just
  2. temperatureunder reflux
  3. temperaturerefluxed for one hour
  4. temperaturecooled
  5. concentrationconcentrated in vacuo
  6. additionpoured into an ice-water mixture
  7. extractionThe resultant aqueous mixture is extracted with ether
  8. washwashed sequentially with saturated ammonium chloride solution and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customto obtain an oil

Quellen und Nachweise

ORD-Eintrag
ord-714e8bfe936743deab83af9dcc78407f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355796B1

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