Acetic Acid → HCID 18699171, compound

Participants

Reaction Steps

Following general procedure J and using 5-amino-7-t-butyl-3,3-dimethyl-2,3-dihydro-benzofuran (Compound 14, 0.55 g, 2.5 mmol), sodium acetate (0.85 g, 6.25 mmol) and sodium borohydride (0.76 g, 20 mmol) in 6.5 mL of ethanol, 6.5 mL of water, 5 mL of acetone (excess) and acetic acid (3.15 g, 52.5 mmol), the title compound (0.62 g, 95%) 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 6.40 (d, 1H, J=2.3 Hz), 6.31 (d, 1H, J=2.3 Hz), 4.17 (s, 2H), 3.58 (heptet, 1H, J=6.3 Hz), 3.00-3.25 (br s, 1H), 1.37(s, 9H), 1.33 s, 6H), 1.24 (d, 6H, J=6.2 Hz).

Provenance & Evidence