Potassium Hydroxide → HCID 19801619, compound

Participants

Reaction Steps

A solution of ethyl N-[2-[2-(diethoxyphosphinyl)ethenyl]phenyl]glycinate (Example 2b)(1.3 g, 3.8 mmol) in diethyl ether (15 ml) is treated with potassium trimethylsilanoate (0.54 g, 4.2 mmol) and stirred over the weekend. The diethyl ether is removed and the oily residue suspended in acetonitrile (50 ml) and stirred under a nitrogen atmosphere for 30 minutes and further treated with trimethylsilylbromide (3 ml) and stirred at room temperature for four hours. 1H-NMR indicates some ester remains so the acetonitrile is removed and the residue is treated with a solution of potassium hydroxide (0.56 g, 10 mmol) in water (3 ml) and stirred for 16 hours. The water is removed and the residue purified on Dowex 50×400 ion exchange resin (water and 2N ammonium hydroxide as eluants). The desired material (fluorescent on tlc under uv light, ninhydrin positive) is obtained from the water eluate as a light, green-white solid (0.12 g).

Provenance & Evidence