Water → (1H-indol-2-yl)methanol

HRID 25159

反応式

HRID 25159 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:16](OCC)=[O:17].O.[OH-].[Na+]>C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[CH2:16][OH:17]

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 73125Ethyl indole-2-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 98783(1H-indol-2-yl)methanol収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of lithium aluminum hydride (10.6 g, 264 mmol) in THF (200 mL) is added dropwise a solution of ethyl indole-2-carboxylate (50.0 g, 256 mmol) in THF (250 mL) over 25 minutes. After 3 h, water (10.6 mL) is carefully added, followed by 15% NaOH (10.6 mL), followed by additional portion of water (31.8 mL). The resulting suspension is dried (Na2SO4) and filtered through celite. After concentration under reduced pressure, the white solid (34.0 g) is crystallized from EtOAc/hexanes to give white needles for 1H-indol-2-ylmethanol. Yield 83%. HRMS (FAB) calcd for C9H9NO+H 148.0762, found 148.0771.

後処理

  1. dry with materialThe resulting suspension is dried (Na2SO4)
  2. filtrationfiltered through celite
  3. concentrationAfter concentration under reduced pressure
  4. customthe white solid (34.0 g) is crystallized from EtOAc/hexanes

出典と根拠

ORDレコード
ord-8e64fb0de175486682f4ed35ca9f9ed1
出典データセット
uspto-grants-2005_02
特許番号
US06858613B2

関連ノート

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