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

HRID 2353360

Reaktionsgleichung

Reaktionsgleichung von HRID 2353360
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-c4438a5e2a234cd480f9e8ee590bbef9
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750021B2

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