p-Toluenesulfonic acid monohydrate → 4-[2-(2-Oxoethyl)-2,3-dihydro-1-benzofuran-5-yl]benzonitrile

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Reaction Steps

A solution of Example 67A (0.5 g, 1.8 mmol) in acetone (10 mL) and p-toluenesulfonic acid monohydrate (0.51 g, 2.7 mmol) was stirred for 45 minutes, diluted with CH2Cl2 (150 mL), washed with cold aqueous sodium bicarbonate (2×100 mL, 10% solution), water (2×100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on silica using CH2Cl2 to give the titled compound (0.41 g, 87%). 1H NMR (CDCl3): 2.95 (m, 2H), 3.65 (m, 3H), 6.82 (d, J=7 Hz, 1H), 7.40 (m, 2H), 7.62 (m, 4H), 9.55(d, J=7 Hz, 1H); MS (DCI) 263 (M+), 281 (M+NH4+).

Provenance & Evidence