Triethylamine → Ethyl acetate hexane

Participants

Reaction Conditions

Reaction Steps

6,7-Dimethoxy-1-methylisoquinolin-3-ol (540 mg) and Et3N (0.9 mL, 2 eq.) in DCM were cooled to −78° C. Tf2O (0.64 mL, 1.2 eq.) was slowly added to the mixture and was stirred for 30 minutes at −78° C. Reaction was then quickly diluted with additional DCM and washed with saturated NaHCO3. Organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 30% EtOAc/hexane yielding product as a white solid (737 mg, 85% yield). 1H NMR (400 MHz) (CDCl3) δ 7.29 (s, 1H), 7.29 (s, 1H), 7.12 (s, 1H), 4.07 (s, 3H), 4.07 (s, 3H), 2.90 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ 156.54, 153.80, 150.67, 135.47, 123.35, 107.62, 105.39, 103.73, 56.23, 56.11, 22.03.

Provenance & Evidence