Hydrochloric Acid → 3-(DIPHENYLPHOSPHINO)PROPIONIC ACID

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Reaction Steps

Diphenylphosphine (2.00 mL, 11.5 mmol) was dissolved in degassed CH3CN (20 mL). Methyl acrylate (3.80 mL, 42.5 mmol) and a few drops of benzyltrimethylammonium hydroxide (40 wt. % in MeOH) were added, and the resulting solution was stirred under Ar(g). The reaction was monitored by TLC and after the introduction of additional drops of base (after 2 h) the reaction was found to be complete after 4 h. The solution was then concentrated under reduced pressure; the resulting oil was dissolved in CH2Cl2 (100 mL) and concentrated again. The resulting oil was then dissolved in MeOH (10 mL) and an aqueous solution of KOH (4.00 g, 71.4 mmol in 10 mL of H2O) was added. The mixture was stirred under Ar(g). After 1 h, the reaction was found to be complete, and the solution was diluted with H2O (200 mL) and acidified to pH 2 with 2M HCl. The suspension was then extracted with CH2Cl2 (2×150 mL), and the organic layers were combined, dried over Na2SO4(s) and concentrated under reduced pressure. The solid residue was purified by silica gel flash chromatography, eluting with 2% MeOH/CH2Cl2, to give the acid 1d as a white solid (2.74 g, 10.6 mmol, 92% yield).

Provenance & Evidence