Reaktion #53367

Reaktionsgleichung

water

Lithium aluminum hydride

II

4-(4-Methoxyphenyl)butylazide

→

III

Ausbeute 94.0%

4-(4-Methoxyphenyl)butylamine

Ausbeute 94.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtration15% NaOH (1.5 mL), then with more water (3 mL) and filtered
2. 2
   WaschenThe solid precipitate was washed with THF
3. 3
   TrocknenThe combined organic fractions were dried over magnesium sulfate
4. 4
   Sonstigethe solvent was removed under reduced pressure

Vorschrift

Lithium aluminum hydride (55 mL of a 1M solution in THF, 0.055 mol) was added drop wise to a solution of II (7.6 g, 0.037 mol) in dry THF (70 mL) at 0° C. and stirred overnight at room temperature in an argon atmosphere. The reaction mixture was treated with water (1.5 mL), then 15% NaOH (1.5 mL), then with more water (3 mL) and filtered. The solid precipitate was washed with THF. The combined organic fractions were dried over magnesium sulfate and the solvent was removed under reduced pressure to give 6.2 g (94%) of III. The purity of III (99%) was determined by GC. 1H NMR (360 MHz, DMSO-d6) δ1.34 (m, 2H), 1.54 (m, 2H), 2.51 (m, 4H), 3.70 (s, 3H), 6.83 (d, J=8.6 Hz, 2H), 7.08 (d, J=8.3 Hz, 2H), 13C (90 MHz, DMSO-d6) δ28.6, 330, 34.1, 41.5, 54.8, 113.1, 129.1, 132.2, 157.3

Quelle