Acetic Acid → HCID 86736643, compound

Participants

Reaction Steps

A solution of [methyl(phenylmethoxy)phosphinyl]acetic acid, methyl ester (1.0 gm., 0.004 mole) in 20 ml. of tetrahydrofuran is added over 50 minutes to a solution of lithium diisopropylamide (0.008 mol.) in tetrahydrofuran maintained at -78° under argon. Following the addition, stirring is continued at -78° for 20 minutes. Phenylmethyl bromide (0.684 gm., 0.004 mol.) in tetrahydrofuran (5 ml.) is then added and the mixture is stirred for 2 hours at -78° and for one hour at 0°. The mixture is then neutralized to pH5 with acetic acid and poured into ether. The ether layer is washed with water, 5% potassium bisulfate and brine, and dried over magnesium sulfate. Evaporation in vacuo yields a residue which is chromatographed on silica gel with dichloromethane/ethyl acetate. The product, [(2-phenylethyl)(phenylmethoxy)phosphinyl] acetic acid, methyl ester (0.66 gm., 50%) is identical by TLC and NMR to that prepared in Example 6.

Provenance & Evidence