Water → 5-(Benzyloxy)-2,3-dihydro-1H-indole

HRID 49492

反応式

HRID 49492 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH3-]C#N.[Na+].O.[OH-].[K+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH2:13][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 146245-BenzyloxyindoleHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 167948815-(Benzyloxy)-2,3-dihydro-1H-indole収率 89.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

In analogy to the method described by Gordon W. Gribble, Joseph H. Hoffmann Synthesis 1977, 859-860, the following reaction was performed. To a precooled solution of 22.3 g (0.1 mol) 5-benzyloxyindole in 270 ml acetic acid, 19 g (0.3 mol) NaCNBH3 were added. The solution was stirred at RT for 2 h, the volume was reduced to one third and poured into 300 ml water. KOH was added under cooling and the solution was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated to yield 20.1 g (89%) 5-Benzyloxy-2,3-dihydro-1H-indole as colorless oil, MS: 225 (M).

後処理

  1. customHoffmann Synthesis 1977, 859-860
  2. customthe following reaction
  3. temperatureunder cooling
  4. extractionthe solution was extracted with ether
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated

出典と根拠

ORDレコード
ord-bd86c4538ce548e0b9203acfa8be0660
出典データセット
uspto-grants-2004_03
特許番号
US06706751B2

関連ノート

読み込み中…