Ethyl indole-2-carboxylate → (1H-indol-2-yl)methanol

HRID 260462

反応式

HRID 260462 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]>O1CCCC1>[OH:17][CH2:16][C:8]1[NH:7][C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2

参加物

4

反応物 2

HCID 73125Ethyl indole-2-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 98783(1H-indol-2-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of lithium aluminum hydride (2.0 g, 0.20 mol) in tetrahydrofuran (100 mL) was cooled with stirring to 0° C. under nitrogen. A solution of ethyl indole-2-carboxylate (10.0 g, 0.052 mol) in tetrahydrofuran was added dropwise, maintaining the reaction temperature between 0°-5° C. After 1 h, the reaction was quenched with saturated sodium potassium tartrate solution. The reaction was filtered and the filter cake washed well with tetrahydrofuran. The tetrahydrofuran was evaporated in vacuo and the residue partitioned between ethyl acetate and water. The ethyl acetate solution was washed with water, saturated brine, dried over magnesium sulfate, filtered and freed of solvent. The title compound was obtained as a yellowish solid. NMR (CDCl3): δ8.18 (1H, bs), 7.57 (1H, d, J=8 Hz), 7.35 (1H, d, J=8 Hz), 7.26 (1H, s), 7.18 (1H, dt, J=1, 8 Hz), 7.10 (1H, dt, J=1, 8 Hz), 6.41 (1H, bs), 4.84 (2H, s).

後処理

  1. temperaturewas cooled
  2. temperaturemaintaining the reaction temperature between 0°-5° C
  3. customthe reaction was quenched with saturated sodium potassium tartrate solution
  4. filtrationThe reaction was filtered
  5. washthe filter cake washed well with tetrahydrofuran
  6. customThe tetrahydrofuran was evaporated in vacuo
  7. customthe residue partitioned between ethyl acetate and water
  8. washThe ethyl acetate solution was washed with water, saturated brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-3e218fb6c0264ff19d79107174dd51dc
出典データセット
uspto-grants-1996_06
特許番号
US05527819

関連ノート

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