Reacción #64034

Ecuación de reacción

hydrochloric acid

aluminum lithium hydride

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

→

(R)-3-ethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene

Rendimiento 95.3%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawith reflux for 12 hours
2. 2
   Temperaturacooled
3. 3
   Extracciónextracted with n-hexane
4. 4
   LavadoThe extract was washed with saturated sodium chloride solution
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated

Procedimiento

To a suspension of aluminum lithium hydride (6.5 g; 0.171 mol) in tetrahydrofuran (100 ml), a solution of (S)-3-(2-chloroethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene ([α]546 --33.4° (C=1.17 in ethanol)) (44.8 g; 0.169 mol) in tetrahydrofuran was dropwise added thereto. The resultant mixture was heated with reflux for 12 hours and then cooled. The cooled mixture was treated with dilute hydrochloric acid and extracted with n-hexane. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to give (R)-3-ethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (37.0 g; 0.161 mol; 94%). B.P., 79°-80° C./0.15 mmHg. [α]546 +2.2° (C=0.95 in ethanol).

Fuente