Triacetoxyperiodinane → 2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalene-1-carbaldehyde

Participants

Reaction Steps

To a solution of Example 179A (0.6 g, 2.3 mmol) in dichloromethane (15 mL) was added Dess-Martin periodanate (1.5 g, 3.5 mmol). The solution was stirred at room temperature for 18 h and then concentrated in vacuo. Column chromatography on silica (10% -20%-30% dichloromethane/hexane) afforded product as a light yellow oil (0.32 g, 53%). 1H NMR (300 MHz, CDCl3) δ ppm 0.63 (m, 1H), 0.76 (dd, J=12.13, 6.62 Hz, 6H), 0.92 (m, 1H), 1.41 (m, 1H), 1.93 (m, 1H), 2.18 (m, 1H), 3.59 (m, 5H), 5.19 (t, J=3.68 Hz, 1H), 7.01 (m, 1H), 7.21 (m, 3H), 9.40 (s, 1H).

Provenance & Evidence