Chloroform → Ethyl (z)-[4-[3-(benzo[b]thiophen-2-yl)-3-(4-trifluoromethylphenyl)allylsulfanyl]-2-methylphenoxy]acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl (Z)-[4-[3-iodo-3-(4-trifluoromethylphenyl)allylsulfanyl]-2-methylphenoxy]acetate (407.1 mg, 0.759 mmol; example 29, step D-E) and (benzo[b]thiophen-2-yl)-tributyltin (327.2 mg, 0.773 mmol, prepared according to Morimoto et al.: J. Med. Chem. 44, 3355 (2001)) in dry N,N-dimethylformamide (3 mL) Pd2(dba)3.CHCl3 (24.1 mg, 0.023 mmol) was added. Traces of moisture and oxygen were removed and 0.20M solution of tri(tert.butyl)phosphine in cyclohexane (0.49 mL, 0.098 mmol) was added under atmosphere of nitrogen and the whole mixture was stirred at 60° C. for 5 h. The dark solution was poured into 10% aqueous solution of potassium fluoride (20 mL) and subsequently ethyl acetate (30 mL) was added. The layers were separated, the aqueous layer was washed with ethyl acetate (2×15 mL) and the collected organic layers were washed with brine (10 mL), 10% solution of potassium fluoride (20 mL), water (20 mL) and brine (20 mL). The organic solution was dried with anhydrous sodium sulfate and its evaporation gave an oil that was purified by column chromatography (silica gel Fluka 60, hexane/ethyl acetate 9:1) yielding 318.6 mg of the ester. Yield: 318.6 mg (76%).

Provenance & Evidence