Methyl 4-methylaminobenzoate → (4-(Methylamino)phenyl)methanol

HRID 63655

Reaktionsgleichung

Reaktionsgleichung von HRID 63655
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 140375Methyl 4-methylaminobenzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 12128786(4-(Methylamino)phenyl)methanolAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-(methylamino)benzoate (2.0 g, 12.1 mmol) in THF (30 mL) was added LAH (6.1 mL, 2.4 M in THF, 14.5 mmol) at 0° C. The reaction was stirred at r.t. for 2 h. The reaction was quenched with EtOAc (50 mL) and water (2 mL). The mixture was dried (Na2SO4) and concentrated. Purification by silica gel chromatography (PE:EtOAc=3:1) gave 1.0 g (60%) of the title compound as a yellow oil. [M+H] Calc'd for C8H11NO, 138. Found 138.

Aufarbeitung

  1. customThe reaction was quenched with EtOAc (50 mL) and water (2 mL)
  2. dry with materialThe mixture was dried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (PE:EtOAc=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-4e687493f3b24096abfc56565926ad9d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447046B2

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