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

HRID 369591

Reaktionsgleichung

Reaktionsgleichung von HRID 369591
[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-02560b88b2444856aaeaa5ab1eef6c63
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140270

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