Tetrahydrofuran → [2-(4-Isobutyl-3-trifluoromethyl-phenyl)-benzooxazol-6-yl]-methanol

HRID 2220273

Reaktionsgleichung

Reaktionsgleichung von HRID 2220273
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[Br-].[CH2:24]([Zn+])[CH:25]([CH3:27])[CH3:26].C1COCC1>Cl>[CH2:24]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20])[CH:25]([CH3:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 68453052{2-[4-Chloro-3-(trifluoromethyl)phenyl]-1,3-benzoxazol-6-yl}methanolHCID 178448254HCID 178448254, Verbindung

Produkt 1

HCID 68453276[2-(4-Isobutyl-3-trifluoromethyl-phenyl)-benzooxazol-6-yl]-methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of [2-(4-chloro-3-trifluoromethyl-phenyl)-benzooxazol-6-yl]-methanol (1 eq) and Pd(PBut3)2 (0.05 eq) is treated with isobutyl zinc bromide in THF (0.5 M, 3 eq). The resulting mixture is heated at 100° C. in microwave for 30 minutes. The reaction mixture is diluted with aqueous HCl (5%) and extracted with EtOAc. The organic solution is washed with brine and dried over Na2SO4. After concentration, the residue is purified by flash column chromatography (30% EtOAc in hexane) to give the desired intermediate [2-(4-isobutyl-3-trifluoromethyl-phenyl)-benzooxazol-6-yl]-methanol. MS: (ES+): 350.1 (M+1)+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic solution is washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe residue is purified by flash column chromatography (30% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7dfa2d220c9e4b939e22386d033ff832
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417065B2

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