Potassium Carbonate → Dimethyl 4-[3-(4-ethoxymethoxy-3-ethylphenyl)propyl]phthalate

Participants

Reaction Conditions

Reaction Steps

5 g (22.7 mmol) of 4-allyl-1-ethoxymethoxy-2-ethylbenzene are dissolved in 100 ml of anhydrous THF, and the medium is cooled to 0° C. 6.6 g (27 mmol) of 9-BBN are added, and the medium is brought to room temperature and then stirred for 12 hours. A solution of 7.8 g (22.6 mmol) of dimethyl 4-trifluoromethanesulphonyloxyphthalate in 100 ml of DMF is added, as well as 6.2 g (44.8 mmol) of potassium carbonate. The reaction medium is degassed with a nitrogen stream, and then 930 mg (1.1 mmol) of dichloropalladium diphosphinoferrocene are added. The medium is heated at 50° C. for 3 hours, and then poured into an ammonium chloride solution and extracted with ethyl acetate. The residue obtained after drying and concentration is purified by chromatography on a silica column (eluent heptane, and then heptane 85/ethyl acetate 15). A yellow oil is obtained (m=6.9 g, y=73%).

Provenance & Evidence