Water → HCID 12968523, compound

Participants

Reaction Steps

Part A: To a solution of 4-methoxybenzenethiol (2.5 g, 17.83 mmol) and ethyl 4-bromobutyrate (3.5 g, 17.83 mmol) in ethanol (50 mL) was cooled on an ice bath and triethylamine (2.73 mL, 19.61 mmol) was added. The solution stirred for 6 hours at ambient temperature. To this solution was added H2O (10 mL) and Oxone® (22 g, 35.7 mmol) and the solution stirred for 20 hours. The solution was filtered to remove excess Oxone® and the filtrate was concentrated in vacuo. The residue was dissolved into H2O and extracted with ethyl acetate. The combined organic layers were washed with saturated NaHCO3 and saturated NaCl and dried over MgSO4. Chromatography (on silica, ethyl acetate/hexane) provided the sulfone as a white solid (2.41 g, 47%). HPLC purity: 97%.

Provenance & Evidence