Reaktion #1689345

Reaktionsgleichung

ethyl 6-cyano-4,4-diphenyl-hexanoate

lithium aluminum hydride

→

desired product

7-Amino-4.4-diphenylheptan-1-ol

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched by a careful addition of water (4.5 mL)
2. 2
   workup.STIRRINGThe mixture was stirred at rt for 10 min
3. 3
   Filtrationfiltered
4. 4
   Waschenthe solid was washed three times with THF
5. 5
   Trocknendried (Na2SO4)
6. 6
   Einengenconcentrated

Vorschrift

To a solution of ethyl 6-cyano-4,4-diphenyl-hexanoate (5.476 g) in anhydrous THF (195 mL) was added portionwise lithium aluminum hydride (LAH) (1.686 g). A large evolution of gas was observed. The mixture was stirred at rt for 1.5 hr. The reaction mixture was quenched by a careful addition of water (4.5 mL), followed by IN NaOH (4.5 mL) and additional water (15 niL). The mixture was stirred at rt for 10 min and then filtered and the solid was washed three times with THF. The organic filtrates were combined, dried (Na2SO4) and concentrated to give the desired product as a solid foam (4.56 g): MS showed (M+H)+ @ 284; 1H-NMR (CDCl3, δ): 1.05-1.3 (m, 4H), 2.0-2.20 (m, 4H), 2.30-2.42 (t, 2H), 2.82-3.0 (t, 2H), 3.0-3.25 (m, 2H), 3.50-3.65 (t, 2H), 5.10-5.20 (broad m, 1H), 6.86-7.36 (m, 14H).

Quelle