Acetic Acid → 3,3-Dimethyl-7-isopropyl-5-(isopropyl)amino-2,3-dihydro-benzofuran

Participants

Reaction Steps

Following general procedure J and using 5-amino-3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran (Compound 13, 0.296 g, 1.5 mmol), sodium acetate (0.53 g, 3.9 mmol) and sodium borohydride (1.47 g, 25 mmol) in 5 mL of ethanol, 5 mL of water, 5 mL of acetone (excess) and acetic acid (1.25 mL, 32.74 mmol), the title compound (0.21 g, 60%) was obtained as an oil which was purified by flash column chromatography using 5% ethyl acetate in hexanes as the eluent. 1H NMR (300 MHz, CDCl3): δ 6.30 (d, 1H, J=2.3 Hz), 6.26 (d, 1H, J=2.3 Hz), 4.14 (s, 2H), 3.54 (heptet, 1H, J=6.3 Hz), 3.03 (heptet, 1H, J=7.0 Hz), 1.29 (s, 6H), 1.22 (d, 6H, J=7.0 Hz), 1.19 (d, 6H, J=6.3 Hz).

Provenance & Evidence