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

HRID 2220273

反応式

HRID 2220273 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
100 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-7dfa2d220c9e4b939e22386d033ff832
出典データセット
uspto-grants-2008_08
特許番号
US07417065B2

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