p-Acetoxybenzoyl chloride → 4-(2-Oxazolyl)phenyl acetate

HRID 1046281

Reaktionsgleichung

Reaktionsgleichung von HRID 1046281
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](Cl)=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Si](N1N=[CH:21][CH:20]=[N:19]1)(C)(C)C>S1(CCCC1)(=O)=O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][CH:21]=[CH:20][N:19]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 2756254p-Acetoxybenzoyl chlorideHCID 27866302-(Trimethylsilyl)-2H-1,2,3-triazole

Produkt 1

HCID 684903404-(2-Oxazolyl)phenyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31347SulfolaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 4-(chlorocarbonyl)phenyl acetate (45.6 g, 0.23 mol) in sulfolane (200 mL) was added 2-TMS-1,2,3-triazole (1.1 eq., 34 mL) over one minute. After stirring for 5 minutes under nitrogen, the reaction was exothermic and the temperature was increased to between 35° C. and 40° C. The reaction mixture was placed under vacuum for 10 minutes to remove the chlorotrimethylsilane (b.p.=57° C.). The reaction mixture was heated at 150° C. for 2.5 hours. After 10 minutes, gas evolution was observed. After cooling, the reaction mixture was poured into water (1.2 L) and extracted with ether (3×). The combined organic layers were washed with water (3×) and brine, dried and concentrated to give 4-(2-oxazolyl)phenyl acetate (44.8 g, 96% th.; 98% pract) as a solid; 1H NMR (CDCl3) δ 8.05 (d, 2H), 7.70 (s, 1H), 7.20 (m, 3H), 2.35 (s, 3H) ppm.

Aufarbeitung

  1. temperaturethe temperature was increased to between 35° C. and 40° C
  2. waitThe reaction mixture was placed under vacuum for 10 minutes
  3. customto remove the chlorotrimethylsilane (b.p.=57° C.)
  4. waitAfter 10 minutes
  5. temperatureAfter cooling
  6. additionthe reaction mixture was poured into water (1.2 L)
  7. extractionextracted with ether (3×)
  8. washThe combined organic layers were washed with water (3×) and brine
  9. customdried
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1f85fe214b8f42cba26e4b1c59a53e33
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569303B2

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