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Hydrochloric Acid → 3-{[4-(5-Fluoro-1-benzofuran-7-yl)phenoxy]methyl}benzoic acid

HRID 928650
ノート
印刷プレビュー

反応式

HRID 928650 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.Br[CH2:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25]C)=[O:24].C(=O)([O-])[O-].[K+].[K+].[OH-].[Li+].Cl>C1COCC1.CO.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:19][C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[C:23]([OH:25])=[O:24])=[CH:13][CH:12]=2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 90384207HCID 90384207、化合物

生成物 1

HCID 903843213-{[4-(5-Fluoro-1-benzofuran-7-yl)phenoxy]methyl}benzoic acid収率 94%

試薬・触媒・溶媒

3
HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To the compound (170 mg, 0.745 mmol) of Step 2, methyl 3-(bromomethyl)benzoate (256 mg, 1.12 mmol), and potassium carbonate (206 mg, 1.49 mmol), DMF (4 mL) was added, and stirred overnight. The solvent was distilled away under reduced pressure, and after diluted with ethyl acetate, the resultant was washed with the water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane/ethyl acetate). To the resulting compound (267 mg, 0.709 mmol), methanol (5 mL) and THF (5 mL) were added. A 1 N lithium hydroxide aqueous solution (1.5 mL) was added thereto under ice-cooling, and stirred at room temperature overnight. After a 1N hydrochloric acid aqueous solution (2 mL) were added thereto under ice-cooling, the solid obtained by concentrating the solvent was collected by filtration to thus obtain the title compound.

後処理

  1. distillationThe solvent was distilled away under reduced pressure
  2. additionafter diluted with ethyl acetate
  3. washthe resultant was washed with the water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate)
  7. temperatureunder ice-cooling
  8. stirringstirred at room temperature overnight
  9. temperatureunder ice-cooling
  10. customthe solid obtained
  11. concentrationby concentrating the solvent
  12. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-18e28a928bdf42fd95870a9f37e562fb
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09290487B2

反応ノート

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