1,3-Dibromopropane → 5-[(4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl)methyl]-2-(3-bromopropyl)-2H-tetrazole

Participants

Reaction Steps

1-[2-Hydroxy-3-propyl-4-((4-(1H-tetrazol-5-ylmethyl)phenoxy)methyl)phenyl]ethanone sodium salt (15 g, 0.039 mol) was added to THF (150 ml) and the minimum amount of lN sodium hydroxide soluton was added to effect solution. 1,3-Dibromopropane (12.12 g, 0.06 mol) was added and the reaction solution was stirred at room temperature for 24 hours. The reaction mixuture was concentrated in vacuo. Water was added to the concentrate and the resultant mixture was extracted with ethyl acetate (3×). The organic layers were combined, washed with water, dried over sodium sulfate, filtered, and concentrated. The resultant residue was chromatographed by HPLC on a silica gel column eluted with a mixture of 9:1 toluene:ethyl acetate to yield 3.0 g of a light yellow oil of the 2H-tetrazole-2-isomer of the above product.

Provenance & Evidence