Tributylamine → Resveratrol

Participants

Reaction Conditions

Reaction Steps

4.5 g of anhydrous aluminium chloride (33.7 mmol) are introduced, under a nitrogen atmosphere, at ambient temperature and with stirring, into 10.37 g of tributylamine (56 mmol) in a three-necked round-bottomed flask. The medium is brought to 60° C. and is maintained at this value for 4 h. 1 g of (E)-3,5,4′-trimethoxystilbene (3.7 mmol) is then introduced and the reaction medium is brought to 80° C. for 2 h and to 100° C. for 2 h. It is brought back to ambient temperature and then 10 g of a 50/50 water/ice mixture are added. It is maintained at 0-5° C. with stirring for 3 h and extracted 4 to 5 times with 10 ml of methyl ethyl ketone. The combined organic phases are washed with 10 ml of a saturated aqueous sodium bicarbonate solution and then with 10 ml of water. After concentrating the organic phase, an HPLC quantitative determination (external calibration) gives an (E)-resveratrol yield of 75%.

Provenance & Evidence