3-(4-Aminophenyl)propionic acid → 4-Aminobenzenepropanol

HRID 1444717

Reaktionsgleichung

Reaktionsgleichung von HRID 1444717
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 754513-(4-Aminophenyl)propionic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 2204244-Aminobenzenepropanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an oven-dried 150 mL round-bottomed flask charged with 3-(4-aminophenyl)propionic acid (Aldrich, 3.0 g, 18.16 mmol) was added THF (50 mL) and lithium aluminum hydride (Aldrich, 1.0M THF solution, 37 mL, 36.32 mmol) at 0° C. The reaction mixture was added Na2SO4.10H2O after 3 h until there was no visible bubbles. The liquid was filtered. The solid was washed with THF and CH2Cl2. The filtrate was dried over Na2SO4. After filtration and concentration in vacuo, the crude was purified by flash chomatography (7% MeOH—CH2Cl2) to provide the title product. MS (ESI): 152 (M+H)+.

Aufarbeitung

  1. filtrationThe liquid was filtered
  2. washThe solid was washed with THF and CH2Cl2
  3. dry with materialThe filtrate was dried over Na2SO4
  4. filtrationAfter filtration and concentration in vacuo
  5. customthe crude was purified by flash chomatography (7% MeOH—CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-0948143fff634beab2c395645f8ae67d
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662811B2

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