Ammonium Chloride → (7-bromo-1-methyl-1H-indol-2-yl)methanol

HRID 12625ノート

反応式

HRID 12625 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([C:12](OCC)=[O:13])=[CH:7]2.[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([CH2:12][OH:13])=[CH:7]2

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 68693640ethyl 7-bromo-1-methyl-1H-indole-2-carboxylate

生成物 1

HCID 68695245(7-bromo-1-methyl-1H-indol-2-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a tetrahydrofuran (40 mL) solution of ethyl 7-bromo-1-methyl-1H-indole-2-carboxylate (1.99 g), lithium tetrahydroborate (463 mg) was added at 0° C., followed by stirring at room temperature for 5 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and saturated saline, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-70:30) to obtain the titled compound having the following physical properties (880 mg).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed in turn with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-70:30)

出典と根拠

ORDレコード
ord-502f3206842346ae9fee5bc68ef8a314
出典データセット
uspto-grants-2010_06
特許番号
US07728023B2

反応ノート

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