Hydrochloric Acid → HCID 69290984, compound

Participants

Reaction Steps

To a solution of 3,5-difluoroanisole (20 g) in THF (200 ml) was added pentamethyldiethylenetriamine (24.05 g). The mixture was cooled to −75° C. n-butyllithium (85 ml, 1.6 M in hexane) was added in such a way that the temperature did not exceed −67° C. The mixture was stirred for 2 h. Ethylglyoxalate (55.5 g, 50% in toluene) was added and the mixture was stirred for a further 2 h. Afterwards, the mixture was allowed to warm up to rt. Water was added and the mixture was made acidic (pH 3) with 25% HCl. The mixture was extracted with EtOAc. The organic phase was washed with 0.5 N HCl, dried, filtered and concentrated. The product was purified by flash chromatography (SiO2, cyclohexane/EtOAc 7:1) to give (RS)-(2,6-difluoro-4-methoxy-phenyl)-hydroxy-acetic acid ethyl ester (13.09 g). Colorless oil. MS 246.1 ([M]+)

Provenance & Evidence