Reacción #64027

Ecuación de reacción

lithium aluminum hydride

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

hydrochloric acid

→

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

Rendimiento 85.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter refluxing for 15 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 aluminum hydride (9.56 g; 0.252 mol) in tetrahydrofuran (70 ml) under a nitrogen stream, a solution of (S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene ([α]546 26.1° (C=1 in n-hexane)) (62.9 g; 0.251 mol) in tetrahydrofuran was dropwise added. After refluxing for 15 hours, the reaction mixture was treated with aqueous tetrahydrofuran in nitrogen, admixed with 5% hydrochloric acid (600 ml) 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 (46.0 g; 0.213 mol; 85%). [α]546 -49.1° (C=1 in chloroform). B.P., 91° C./0.5 mmHg.

Fuente