Methyl iodide → HCID 14234360, compound

Participants

Reaction Steps

To a mixture of 9 g of 35% potassium hydride in oil, prewashed with hexane, and 40 mL of tetrahydrofuran was added 4.05 g of 5-hydroxymethyl-9-methoxy-3-n-propyl-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one. The mixture was stirred at room temperature for 30 minutes, and then heated under reflux for 30 minutes. Methyl iodide (8 mL) was added to the cooled mixture which was then heated under reflux for one hour. Excess hydride was destroyed by addition of 10 mL of methanol, and the solvent was removed. The product was taken up in methylene chloride/water, and the aqueous layer was extracted with methylene chloride. Removal of the solvent gave 4.45 g of 9-methoxy-5-methoxymethyl-3-n-propyl-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one. NMR spectrum (δ in CDCl3); 6.8 (m, 2H); 6.5 (m, 1H); 4.5 (s, 1H); 3.9 (s, 3H); 3.3 (s, 3H) and 1.0 (t, 3H), among others.

Provenance & Evidence