Water → HCID 7174672, compound

Participants

Reaction Steps

A mixed solvent (volume ratio=1:1, 5 mL) of water and formic acid and a chiral iridium aqua complex represented by the formula (12-R) (0.5 mol % relative to 2-methylphenylglyoxylic acid) were mixed, and 2-methylphenylglyoxylic acid (1 mmol) was added to the obtained solution at room temperature. The obtained mixture was stirred at room temperature to carry out asymmetric transfer hydrogenation. After confirming the disappearance of 2-methylphenylglyoxylic acid by thin layer chromatography, the reaction was quenched with brine (20 mL). The reaction mixture was subjected to extraction treatment (three times) with ethyl acetate (20 mL), and the obtained organic layers were combined. The combined organic layer was dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=20:1) to give the corresponding (R)-2-(2-methylphenyl)-2-hydroxyacetic acid. Yield 95%, optical purity 83% e.e.

Provenance & Evidence