Hydrochloric Acid → 7-Chloro-2-(2-hydroxymethylbenzofuran-5-yl)quinoline

HRID 2258515ノート

反応式

HRID 2258515 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[CH:13]=[CH:14][C:15]4[O:19][C:18]([C:20](OC)=[O:21])=[CH:17][C:16]=4[CH:24]=3)=[N:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[CH:13]=[CH:14][C:15]4[O:19][C:18]([CH2:20][OH:21])=[CH:17][C:16]=4[CH:24]=3)=[N:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 229221827-Chloro-2-(2-methoxycarbonylbenzofuran-5-yl)quinoline

生成物 1

HCID 229222147-Chloro-2-(2-hydroxymethylbenzofuran-5-yl)quinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 7-chloro-2-(2-methoxycarbonylbenzofuran-5-yl)quinoline (0.92 g) in tetrahydrofuran (10 ml), lithium aluminum hydride (76.7 mg) was added dropwise under ice cooling. After being stirred for 2 hours, the resulting mixture was poured into a mixture of ice and diluted aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and toluene. The fractions containing object compound were combined, concentrated under reduced pressure, and recrystallized from toluene to give 7-chloro-2-(2-hydroxymethylbenzofuran-5-yl)quinoline (0.58

後処理

  1. additionwas added dropwise under ice cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with a mixture of ethyl acetate and toluene
  7. additionThe fractions containing object compound
  8. concentrationconcentrated under reduced pressure
  9. customrecrystallized from toluene

出典と根拠

ORDレコード
ord-988932bb048d42f0970fe16d23392df4
出典データセット
uspto-grants-1997_08
特許番号
US05661159

反応ノート

読み込み中…