Triacetoxyperiodinane → (R)-3-(Benzyloxy)-2-(4-bromo-2-methylphenyl)propanal

Participants

Reaction Steps

To 16F (2.83 g, 8.44 mmol) in dichloromethane (60 ml) was added Dess-Martin periodinane (4.30 g, 10.13 mmol) at rt. The reaction was stirred at rt for 2 h. The mixture was filtered and the filtrate was concentrated. The crude product was purified by flash chromatography (0-30% ethyl acetate/hexanes). The desired fractions were combined, concentrated to give 16G (2.0 g, 6.00 mmol, 71.1% yield) as colorless oil. MS (ESI) (m/z): 331.3, 333.3 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ ppm 9.72 (s, 1H) 7.40 (d, J=1.77 Hz, 1H) 7.24-7.38 (m, 6H) 6.95 (d, J=8.08 Hz, 1H) 4.46-4.61 (m, 2H) 4.02-4.16 (m, 2H) 3.67-3.81 (m, 1H) 2.34 (s, 3H).

Provenance & Evidence