Dimethylformamide → 3-Ethyl-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-dihydroxybenzene

Participants

Reaction Steps

To a solution of 13 (0.15 g, 0.268 mmol) in methanol (2 mL), acetic acid was added acetic acid (0.032 mL, 0.563 mmol) followed by potassium fluoride (0.033 mg, 0.563 mmol). Dimethylformamide was then added (0.5 mL) and the mixture was stirred for 16 hours then more acetic acid (0.04 mL) and KF (0.033 mg) were added and the mixture stirred for 48 hours. The mixture was then diluted with tertbutylmethyl ether (50 mL) and washed with water (10 mL). The aqueous layer was re-extracted, the combined organic layers were washed with brine, dried over sodium sulphate and the solvent removed under reduced pressure to give a crude which was purified by column (cyclohexane:AcOEt 8:2+1% AcOH) to give 0.05 g of ZSB-76:

Provenance & Evidence