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

HRID 49492

반응식

HRID 49492 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bd86c4538ce548e0b9203acfa8be0660
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706751B2

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