4-Fluorobenzamide → Ethyl[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetate

HRID 227449

Reaktionsgleichung

Reaktionsgleichung von HRID 227449
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH:12]([CH3:21])[C:13](=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1(C)C=CC=CC=1>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[O:7][C:12]=1[CH3:21])[CH3:19]

Komponenten

4

Edukt 2

HCID 715724-FluorobenzamideHCID 12780443Ethyl 4-bromo-3-oxopentanoate

Produkt 1

HCID 85817159Ethyl[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetateAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A suspension of 4fluorobenzamide (12.9 g) and ethyl 4bromo-3-oxopentanoate (Chem Abs No. 3618769-6; 5.24 g) in anhydrous toluene (120 ml) was heated at 140° C. for 19 h, using a Dean-Stark trap. The solution was allowed to cool, filtered, and the residual solid washed with toluene (30 ml). The combined filtrate and washings were concentrated in vacuo to give a brown oil, which was purified by Biotage flash chromatography on silica gel (90 g column), eluting with ethyl acetate:cyclohexane (5:95, 7.5:92.5, 10:90), to give the title compound as a yellow solid (2.98 g).

Aufarbeitung

  1. temperatureto cool
  2. filtrationfiltered
  3. washthe residual solid washed with toluene (30 ml)
  4. concentrationThe combined filtrate and washings were concentrated in vacuo
  5. customto give a brown oil, which
  6. customwas purified by Biotage flash chromatography on silica gel (90 g column)
  7. washeluting with ethyl acetate:cyclohexane (5:95, 7.5:92.5, 10:90)

Quellen und Nachweise

ORD-Eintrag
ord-4a4170c5aeee4106806b662e8d978de3
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560548B2

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