Potassium Iodide → (3-Hydroxy-4-methoxybenzyl)-6-methoxy-2-(3-methylbut-2-enyl)-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Steps

1.38 g. (4.37 mmol) (-)-7-Hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline in 25 ml. anhydrous ethanol is mixed with 0.9 g. (10.7 mmol) sodium bicarbonate, 0.44 g. (4.2 mmol) 1-chloro-3-methylbut-2-ene and 100 mg. potassium iodide. The reaction mixture is allowed to react for 1 hour at ambient temperature and for 4 hours at 80° C. The usual working up and chromatographic purification on silica gel with chloroform as elution agent gives (3-hydroxy-4-methoxybenzyl)-6-methoxy-2-(3-methylbut-2-enyl)-1,2,3,4-tetrahydroisoquinoline in the form of a yellowish foam.

Provenance & Evidence