Phenacyl bromide → HCID 18628686, compound

Participants

Reaction Steps

A solution comprised of ethyl 4-methyl-2-thiocarbamoylpentanoate (410 mg, 2 mmol) in ethanol (5 mL) was treated with 2-bromo-1-phenylethanone (400 mg, 2 mmol). The mixture was refluxed for 30 minutes and concentrated to provide ethyl 4-methyl-2-(4-phenylthiazol-2-yl)pentanoate as a crude product. The crude product was dissolved in methanol (5 mL, tech. grade) and the solution was treated with sodium hydroxide (100 mg, 2.5 mmol). The mixture was stirred for 2 hours and diluted with 0.1 M hydrochloric acid solution. The dilution was extracted with ethyl acetate (25 mL) and the extract was washed with water and brine, dried (MgSO4) and concentrated. Product was purified from the residue by flash column on silica gel (60° A) with 33% ethyl acetate in hexane to provide 4-methyl-2-(4-phenylthiazol-2-yl)pentanoic acid (500 mg, 1.8 mmol). Rf 0.33. 1H NMR (DMSO-d6): 0.96 (d, 6H), 1.71-1.79 (m, 3H), 3.61 (m, 1H), 7.12 (s, 1H), 7.32-7.41 (m, 5H). LCMS: 275.91 (M+H+).

Provenance & Evidence