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

HRID 52471

Reaktionsgleichung

Reaktionsgleichung von HRID 52471
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d7a29701302b4fd1acecb69f4414482f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616586

Verknüpfte Notizen

Wird geladen…