Glyoxylic Acid → (Ethoxy-phenyl-phosphinoyl)-hydroxy-acetic acid ethyl ester

Reaction equation

C([P:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[O-:4])C.C(N([CH2:17][CH3:18])CC)C.[C:19]([OH:23])(=[O:22])[CH:20]=[O:21].[C:24]1(C)C=CC=C[CH:25]=1>>[CH2:24]([O:22][C:19](=[O:23])[CH:20]([P:3]([O:5][CH2:17][CH3:18])([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:4])[OH:21])[CH3:25]

Participants

Reactant 4

HCID 760Glyoxylic Acid

HCID 1140Toluene2×

HCID 8471Triethylamine

HCID 19040357Ethyl(phenyl)phosphinate

Product 1

HCID 69524884(Ethoxy-phenyl-phosphinoyl)-hydroxy-acetic acid ethyl esterYield 48%

Procedure

To a solution of ethylphenylphosphinate (0.5 g, 2.94 mmol) in 5 mL of anhydrous toluene and anhydrous triethylamine (0.17 mL, 1.18 mmol) under argon was added 0.68 g (2.94 mmol) of a 50% (w/w) glyoxylic acid solution in toluene. The mixture was stirred for 16 h at room temperature, at which point the solvent was removed in vacuo. The crude material was purified by flash chromatography on silica gel. Elution with 100% ethylacetate afforded 383 mg (48%) of the desired compound.