Reaktion #53405

Reaktionsgleichung

water

Lithium aluminum hydride

2

4-(4-Methoxyphenyl)butylazide

→

3

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 (LAH) (55 mL of a 1.0 M solution in THF, 0.055 mol) was added drop wise to a solution of 2 (7.6 g, 0.037 mol) in dry THF (70 mL) at 0° C. The mixture was stirred overnight at room temperature in an argon atmosphere then the 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 3. The purity of 3 (99%) was determined by GC. 1H NMR (360 MHz, DMSO-d6) δ 1.34 (m, 2H), 1.54 (m, 2H), 2.51 (m, 4H), 3.70 (s, 3H), 6.83 (d, 2H), 7.08 (d, 2H). 13C (90 MHz, DMSO-d6) δ 628.6, 330, 34.1, 41.5, 54.8, 113.1, 129.1, 132.2, 157.3

Quelle