Oxolane--water (1/1) → HCID 66745597, compound

Participants

Reaction Steps

To a solution of 2-(cyclohex-2-en-1-yloxy)-6-nitrobenzonitrile (Example 133e, 5.3 g, 21.7 mmol) in THF/H2O (1:1 by volume, 110 mL) was added OsO4 (110.3 mg, 0.434 mmol) at room temperature. After it was stirred for 30 minutes, NaClO3 (2.71 g, 26.04 mmol) was added in small portions over a period of 1 h, and the reaction mixture was stirred at room temperature for 48 h. The reaction was carefully quenched with aqueous sodium bisulfite solution, and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated. The residue was purified by chromatography on silica gel eluting with 80-100% EtOAc in hexanes to give the title compound as a brown solid (3.88 g, 64%). MS 279 (MH+).

Provenance & Evidence