Sodium Cyanide → HCID 90409313, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1-(2-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzene-sulfonate (230 mg, 0.495 mmol), Bu4NI (2 mg, 4.95 μmol), and NaCN (73 mg, 1.49 mmol) in DMSO (10 mL) was stirred at 135° C. under N2 for 20 h, then cooled to rt. The reaction was diluted with EtOAc (10 ml) and washed with water (20 ml×4). The organic layer was concentrated in vacuo to give a crude brown oil, which was purified by flash chromatography (SiO2) using a gradient from 0% to 30% EtOAc/hexane (20 min) to give the title compound (150 mg, 0.470 mmol, 95% yield) as a clear oil. LCMS [M+Na]+=342.1. 1H NMR (CDCl3) δ: 7.77-7.72 (dd, J=7.7, 1.9 Hz, 1H), 7.38-7.33 (m, 2H), 7.22-7.16 (m, 1H), 7.15-7.10 (m, 2H), 7.01-6.95 (m, 2H), 6.83-6.79 (dd, J=8.0, 1.3 Hz, 1H), 3.98 (s, 2H), 2.70-2.58 (m, 2H), 2.22 (s, 2H), 2.05-1.94 (m, 2H), 1.88-1.74 (m, 4H).

Provenance & Evidence