Dimethylformamide → HCID 91185488, compound

Participants

Reaction Steps

Phosphorus trichloride (0.1 ml of a solution containing 0.17 ml/ml in dry dichloromethane) was added to a stirred, ice bath cooled, mixture of the sulphoxide from Example 5 (55 mg) and dry dimethylformamide (0.05 ml) in dry dichloromethane (2 ml). After stirring for 15 minutes at ice bath temperature the mixture was diluted with ethyl acetate (10 ml) and was washed with satd NaHCO3 (2 ml), and brine (3×2 ml). The dried (MgSO4) organic layer was evaporated and the residue was chromatographed on silica gel eluting with ethyl acetate/hexane mixtures to give the title compound as an amorphous solid (45 mg), d ppm (CDCl3) 1.42-1.58 (1H, m), 1.79-1.95 (2H, m), 2.21-2.33 (1H, m), 3.24 (1H, d, J 18.7 Hz), 3.56-3.66 (3H, m), 3.71-3.92 (2H, m), 4.84 (1H, dd, J 9.2 and 6.6 Hz), 4.95 (1H, d, J 4.8 Hz), 5.85 (1H, dd, J 9.1 and 4.8 Hz), 6.04 (1H, d, J 9.1 Hz), 6.86 (1H, s), 7.25-7.42 (15H, m).

Provenance & Evidence