Methyl iodide → (+/-)-2-Dodecyl-alpha-methyl-alpha-phenyl-2H-tetrazole-5-acetic acid

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Reaction Steps

To a THF solution (30 mL) of n-BuLi (0.0055 mol, 1.6M in hexanes) at -78° C. under N2 with stirring was added 1.0 g (0.00027 mol) of (±)-2-dodecyl-α-phenyl-2H-tetrazole-5-acetic acid (Compound d, Example 13). The resulting yellow solution was stirred at -78° C. for 30 minutes before iodomethane (0.34 mL, 0.0055 mol) was added. This solution was stirred for 3 hours before quenching with 1N HCl (20 mL). The mixture was then partitioned between ethyl acetate and water. The organic phase was washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 1.12 g of pure product.

Provenance & Evidence