Dimethyl Sulfide → HCID 20781254, compound

Participants

Reaction Steps

Ozone was bubbled through a solution of the product of Example 79 (2.5 g, 4.9 mmol) in dichloromethane/methanol (125 ml/25 ml) at −78° C. until a blue colour was observed. Oxygen was bubbled through the mixture for 10 minutes until the blue colour disappeared. The mixture was quenched with dimethyl sulfide (2.16 ml, 29.5 mmol), allowed to warm to room temperature and stirred for 16 hours. The mixture was concentrated in vacuo to give an oil (2.80 g), which was chromatographed on silica, eluting with 20% ethyl acetate/isohexane to give the aldehyde (2.18 g, 87%). 1H NMR (CDCl3, 360 MHz): 1.59-1.70 (2H, m), 2.04-2.09 (2H, m), 2.48 (2H, t, J=12.3), 2.61-2.68 (2H, m), 3.82 (1H, m), 5.75 (1H, d, J=7.7), 6.77-6.86 (1H, m), 7.07-7.11 (2H, m), 7.57 (2H, d, J=8.1), 7.90 (2H, d, J=8.3), 10.10 (1H, s)

Provenance & Evidence