Diisobutylaluminumhydride → 4-Phenyl-but-3-enylamine

HRID 6714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 6714
[C:1]1([CH:7]=[CH:8][CH2:9][C:10]([NH2:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[C:1]1([CH:7]=[CH:8][CH2:9][CH2:10][NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 540149774-Phenyl-but-3-enoic acid amide

Produkt 1

HCID 537132274-Phenyl-but-3-enylamineAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of 4-phenyl-but-3-enoic acid amide (5.0 g, 31 mmol) in 250 mL dichloromethane was cooled to 0° C. Diisobutylaluminum hydride (1 M in dichloromethane, 250 mL) was added and the resulting homogeneous mixture was allowed to slowly warm to rt. The reaction was stirred for 4 days then quenched by carefully pouring the mixture onto 200 mL of 1:1 water/methanol at 0° C. The aluminum salts were removed by filtration and washed with methanol. The combined filtrate was collected and the volatile material was removed by a rotary evaporator to give of 4-phenyl-but-3-enylamine (3.62 g, 79%) as a pale yellow oil.

Aufarbeitung

  1. temperatureto slowly warm to rt
  2. customthen quenched
  3. additionby carefully pouring the mixture onto 200 mL of 1:1 water/methanol at 0° C
  4. customThe aluminum salts were removed by filtration
  5. washwashed with methanol
  6. customThe combined filtrate was collected
  7. customthe volatile material was removed by a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-66725a1049364b39b741a7bdee9695b0
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084154B2

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