Water → (1,2,3,4-Tetrahydroquinolin-2-yl)methanol

HRID 862560

Reaktionsgleichung

Reaktionsgleichung von HRID 862560
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([CH:11]1[CH2:20][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[CH2:20][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 Hydroxide2×HCID 2736972Methyl 1,2,3,4-tetrahydroquinoline-2-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 15052240(1,2,3,4-Tetrahydroquinolin-2-yl)methanolAusbeute 106,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a suspension of LiAlH4 (8.3 g, 0.22 mol) in THF (200 mL) was added dropwise 2-methoxycarbonyltetrahydroquinoline (42 g, 0.22 mol) in THF (200 mL) at 0° C. The mixture was stirred for 3 h at room temperature and refluxed for 0.5 h. The excess reagent was decomposed by addition of aqueous sodium hydroxide in THF. To the mixture was added 1N aqueous NaOH, water, and diethyl ether, successively. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated to give 38.4 g of 2-hydroxymethyltetrahydroquinoline (quant).

Aufarbeitung

  1. temperaturerefluxed for 0.5 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-edf4c1abe13443eb986d015ad3f7fc81
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05719152

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