Tributylstannane → HCID 21833714, compound

Participants

Reaction Steps

A stirred solution of 4-(2-(2-iodophenoxy)ethyl)-1-methyl-1,2,3,6-tetrahydropyridine (D100, 6.3 g, 0.018 mole) and AIBN (50 mg) in benzene (700 ml) was heated to reflux under argon, then treated dropwise over 1 h with a solution of tributyltin hydride (9.7 ml, 0.036 mole) in benzene (100 ml). The reaction mixture was heated under reflux for a further 3 h after completing the addition, then more tributyltin hydride (3.8 ml, 0.014 mole) and AIBN (30 mg) were added and heating under reflux was continued for 4 h. The reaction mixture was allowed to cool, then concentrated in vacuo and the residue treated with 2M HCl acid (150 ml), washed with ethyl acetate (100 ml), basified with potassium carbonate and extracted with ethyl acetate (2×100 ml). The combined extract was dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was chromatographed on silica gel eluting with 0 to 2% methanol/chloroform to afford the title compound (2.3 g of approx. 86% purity, 51%).

Provenance & Evidence