Water → 2,3-dihydro-1H-indol-2-ylmethanol

HRID 52471

반응식

HRID 52471 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12]1)=O.[OH-].[Na+].O>C1COCC1.C(OCC)C>[OH:8][CH2:9][CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12]1

참가 물질

7

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2794655Methyl indoline-2-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 27946642,3-dihydro-1H-indol-2-ylmethanol수율 96%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of LiAlH4 (4.65 g, 0.122 mol) in THF (100 mL) was added dropwise 2-methoxycarbonylindoline (10.85 g, 0.0613 mol) in THF 260 mL at room temperature. The mixture was refluxed for 3.5 h and then excess reagent was decomposed by addition of aqueous THF. To the mixture was added 1N aqueous NaOH (50 mL), water (100 mL), and diethyl ether (100 mL), successively. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated to give 8.77 g of 2-hydroxymethylindoline (96%): 1H NMR (270 MHz, CDCl3) δ7.08 (d, 1H, J=7 Hz), 7.02 (t, 1H, J=7 Hz), 6,71 (t, 1H, J=7 Hz), 6.64 (d, 1H, J=7 Hz), 4.02 (m, 1H), 3.70 (dd, 1H, J=11, 4 Hz), 3.56 (dd, 1H, J=11, 7 Hz), 3.09 (dd, 1H, J=16, 9 Hz), 2.81 (dd, 1H, J=16, 8 Hz).

후처리

  1. temperatureThe mixture was refluxed for 3.5 h
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d7a29701302b4fd1acecb69f4414482f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616586

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