Carbon Tetrachloride → HCID 70317767, compound

Participants

Reaction Steps

Triphenyl phosphine (0.32 g, 1.2 mmol), followed by carbon tetrachloride (0.06 ml, 0.60 mmol), were added to a solution of the product from Example 80 (0.16 g, 0.30 mmol) in acetonitrile (1.5 ml). The mixture was stirred for 1.5 hours, additional carbon tetrachloride (0.18 ml, 0.18 mmol) was added, and the mixture was stirred for 0.5 hours, diluted with water (10 ml) and extracted with diethyl ether (2×10 ml). The combined organic phases were washed with brine (sat. 20 ml), dried (magnesium sulfate) and evaporated in vacuo. The crude product was chromatographed on silica, eluting with 20% ethyl acetate/isohexane to give the nitrile (0.11 g, 71%). 1H NMR (CDCl3, 360 MHz): 1.63-1.69 (2H, m), 2.04-2.09 (2H, m), 2.48 (2H, bt, J=13.0), 2.59-2.64 (2H, m), 3.81 (1H, m), 5.66 (1H, d, J=7.3), 6.79-6.86 (1H, m), 7.07-7.13 (2H, m), 7.52 (2H, d, J=8.5), 7.70 (2H, d, J=8.5)

Provenance & Evidence