Reacción #64029

Ecuación de reacción

lithium hydride

aluminum lithium hydride

hydrochloric acid

(S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene

→

(S)-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene

Rendimiento 73.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawhile refluxing for 36 hours
2. 2
   Extracciónextracted with n-hexane
3. 3
   LavadoThe extract was washed with saturated sodium chloride solution
4. 4
   Otrodried
5. 5
   Concentraciónconcentrated
6. 6
   workup.DISTILLATIONdistilled

Procedimiento

To a suspension of lithium hydride (4.52 g; 0.569 mol) and aluminum lithium hydride (1.81 g; 0.048 mol) in tetrahydrofuran under nitrogen, (S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (94.69 g; 0.378 mol) was added dropwise, and the resultant mixture was heated while refluxing for 36 hours. The reaction mixture was treated with dilute hydrochloric acid and extracted with n-hexane. The extract was washed with saturated sodium chloride solution, dried, concentrated and distilled to give (S)-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (59.7 g; 0.276 mol).

Fuente