Aluminum(III) Chloride → HCID 15101112, compound

Participants

Reaction Steps

To a stirring suspension of lithium aluminum hydride (9.24 g) in 250 ml of dry tetrahydrofuran under nitrogen is added dropwise a solution of aluminum chloride (10.82 g) in 250 ml of diethyl ether. The mixture is stirred at room temperature for 20 minutes and a solution of 1-(1,4-dioxaspiro-[4,5]-dec-8-ylacetyl)-1,2,3,6-tetrahydro-4-phenylpyridine (27.70 ) (Example Ia) in 500 ml of tetrahydrofuran is added dropwise. The resulting mixture is stirred at room temperature for 12 hours. The reaction is quenched by careful addition of 10 ml of water. After 30 minutes, 44 g of a 25% solution of sodium hydroxide is added dropwise and the mixture stirred for one additional hour. The inorganic salts are filtered through Celite and the filtrate evaporated in vacuo, taken up into 250 ml of a 10% solution of hydrochloric acid and 250 ml of acetone and refluxed for eight hours. The solution is cooled, concentrated in vacuo to remove the acetone, made basic with ammonium hydroxide, and extracted with chloroform (2×250 ml). The organic extracts are pooled, dried over magnesium sulfate, and evaporated to give a semisolid residue which is triturated with 100 ml of diethyl ether and filtered. The title compound is obtained (16.82 g) as a light yellow solid; mp 94°-96° C.

Provenance & Evidence