Isopropanol → 4-Oxetan-3-yl-3-(2-m-tolyl-ethoxy)-benzoic Acid Isopropyl Ester

Participants

Reaction Steps

2.0 g of 4-borono-3-(2-m-tolyl-ethoxy)-benzoic acid methyl ester, 51 mg of nickel iodide, 2.0 g of sodium bis(trimethylsilyl)amide and 25 mg of trans-2-aminocyclohexanol hydrochloride were placed into a microwave vial and 10 ml of anhydrous 2-propanol added. The mixture was stirred for 10 min. Then a solution of 1.0 g of 3-iodo-oxetane in 3 ml of anhydrous 2-propanol was added and the mixture reacted for 40 min at 80° C. under microwave irradiation. The mixture was then poured into 150 ml of EA and washed three times with 30 ml each of a saturated aqueous sodium hydrogensulfate solution and three times with 30 ml each of a saturated aqueous sodium carbonate solution. The organic layer was dried with magnesium sulfate and evaporated. Silica gel chromatography (EA/HEP 1:5) of the residue yielded 120 mg of the title compound.

Provenance & Evidence