Propargyl alcohol → 5-Benzyloxy-2-(3-hydroxy-prop-1-ynyl)-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-Benzyloxy-2-bromo-benzoic acid methyl ester (120 g, 374 mmol) and prop-2-yn-1-ol (41.9 g, 747 mmol) in triethylamine (1 L), copper(I) iodide (0.712 g, 3.74 mmol) and bis(triphenylphosphine)palladium(II) chloride (26.2 g, 37.4 mmol) at RT under N2. The mixture was heated at 50° C. reflux under N2 for 12 hr. The reaction was cooled to room temperature, concentrated to dryness, diluted with H2O (50 mL) and extracted with ethyl acetate (500 mL*3), The organic phase was washed with saturated sodium bicarbonate solution 500 mL, dried over Na2SO4. After concentration, the crude product was purified by silica gel chromatography eluted with PE:EA=10:1˜4:1 to give title product (80 g, 72%) as yellow oil.

Provenance & Evidence