Hydrochloric Acid → HCID 21968637, compound

Participants

Reaction Conditions

Reaction Steps

14 g (67.96 mmol) of (+)-2,3-dimethyl-7-(2-hydroxy-1(S)-hydroxyethyl)benzofuran and 250 ml of pyridine are introduced into a 500 ml three-necked flask. The mixture is cooled to 0° C. and 11.62 g (61.16 mmol) of tosyl chloride and then 0.5 g of dimethylaminopyridine are added. The reaction mixture is stirred for 2 h at room temperature, 0.645 g of tosyl chloride is added and stirring is continued for 16 h. The mixture is cooled to 0° C. and 300 ml of ethyl acetate and then 250 ml of a hydrochloric acid solution (4M) are added. Extraction is carried out with ethyl acetate (2×400 ml). The organic phases are combined, washed with 2×250 ml of a hydrochloric acid solution (4M), dried over magnesium sulphate and concentrated. The residue is purified by silica column chromatography (elution solvent: 25% ethyl acetate in cyclohexane). 15 g of (+)-2,3-dimethyl-7-(2-para-methylphenylsulphonyl-1(S)-hydroxyethyl)benzofuran are obtained in the form of a white solid--M.p.: 90° C.

Provenance & Evidence