Hydrochloric Acid → 5-Amino-3,3-dimethyl-7-isopropyl-2,3-dihydrobenzofuran

Participants

Reaction Steps

Following general procedure D and using 5-bromo-3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran (Compound 8, 0.268 g, 1 mmol), benzophenone imine (0.199 g, 1.1 mmol), sodium-tert-butoxide (0.134 g, 1.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.021 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.040 g, 0.064 mmol) in 5 mL of anhydrous toluene, followed by hydrolysis of the intermediary imine with 2M hydrochloric acid in tetrahydrofuran, the title compound was obtained as an oil (0.131 g, 69%). 1H NMR (300 MHz, CDCl3): δ 6.39 (d, 1H, J=2.3 Hz), 6.33 (d, 1H, J=2.3 Hz), 4.15 (s, 2H), 3.32 (br s, 2H), 3.03 (heptet, 1H, J=6.9 Hz), 1.28 (s, 6H), 1.22 (d, 6H, J=6.9 Hz).

Provenance & Evidence