Methyl iodide → 2-[5-Fluoro-3-(trifluoromethyl)phenyl]-4-(3-iodopropyl)-1,3-oxazole

HRID 1694655

Reaktionsgleichung

Reaktionsgleichung von HRID 1694655
[F:1][C:2]1[CH:3]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:5]=[C:6]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][CH2:14][CH2:15]O)[N:12]=2)[CH:7]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.C[I:45]>>[F:1][C:2]1[CH:3]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:5]=[C:6]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][CH2:14][CH2:15][I:45])[N:12]=2)[CH:7]=1

Komponenten

4

Edukt 3

HCID 6328Methyl iodide2×HCID 8289Triphenyl PhosphateHCID 672791633-{2-[5-Fluoro-3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl}propan-1-ol

Produkt 1

HCID 672790242-[5-Fluoro-3-(trifluoromethyl)phenyl]-4-(3-iodopropyl)-1,3-oxazoleAusbeute 34 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To 3-{2-[5-fluoro-3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl}propan-1-ol (250.3 mg, 0.865 mmol) was added a mixture of triphenyl phosphate (295.4 mg, 0.952 mmol, 1.1 equiv.) and methyl iodide (184.2 mg, 1.298 mmol, 1.5 equiv.). The mixture was heated at 130° C., while adding a further amount of methyl iodide (184.2 mg, 1.298 mmol, 1.5 equiv.). The reaction mixture was heated for a total of 2 hours, and then purified by column-chromatography (SiO2=25 g, hexane/EtOAc=7:1) followed by preparative TLC (SiO2=6 plates, hexane/EtOAc=15:1) to give 2-[5-fluoro-3-(trifluoromethyl)phenyl]-4-(3-iodopropyl)-1,3-oxazole (116.1 mg, 0.291 mmol, 34%) as a colorless oil.

Aufarbeitung

  1. temperatureThe reaction mixture was heated for a total of 2 hours
  2. custompurified by column-chromatography (SiO2=25 g, hexane/EtOAc=7:1)

Quellen und Nachweise

ORD-Eintrag
ord-740f7282bde442ce854a893954f711be
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158810B2

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