Propan-2-one--water (1/1) → HCID 22177240, compound

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Reaction Steps

A mixture of 2-(4-iodo-phenyl)-pent-4-enenitrile (2.8 g, 9.9 mmol, intermediate for preparing EXAMPLE 2), OsO4 (0.7 mL, 4% in water, 0.10 mmol), and NaIO4 (4.44 g, 20.8 mmol) in 2:1 acetone/H2O (100 mL) was stirred at room temperature for 16 h. TLC (1:1 hexanes/EtOAc) showed no starting material left. The mixture was diluted with H2O (50 mL) and extracted with CH2Cl2 (50 mL×4). The organic layer was washed with brine, dried (Na2SO4) and concentrated by rotary evaporation. Purification by silica gel chromatography (1:1 hexanes/EtOAc) gave 2-(4-iodo-phenyl)-4-oxo-butyronitrile as a yellowish oil, 1.9 g (68%). 1H NMR (300 MHz, CDCl3): δ 9.85 (s, 1H), 7.84 (d, 2H), 7.24 (d, 2H), 4.44 (t, 1H), 3.33 (dd, 1H), 3.14 (dd, 1H).

Provenance & Evidence