Ammonium nitrate → HCID 86751439, compound

Participants

Reaction Steps

To a stirred solution of 1-(1,3-dithian-2-yl)-3-(4-fluorophenoxy)cyclopentane (10.0 g, 33.5 mmol) in 75% aqueous acetonitrile (300 ml) was added eerie ammonium nitrate (J. Chem Soc., Chem. Commun., 1977, 680) (74.0 g, 135 mmol) at room temperature. The reaction mixture was stirred for 0.5 h at the same temperature, diluted with water (500 ml) and then extracted with ether (500 ml). The ether phase was washed with brine (300 ml), dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography {SiO2, 250 g; hexane/ethyl acetate (10:1)} gave 1.28 g (20%) of cis-3-(4-fluorophenoxy)cyclopentanecarbaldehyde (Rf=0.2), 2.35 g (37%) of trans-3-(4-fluorophenoxy)cyclopentanecarbaldehyde (Rf=0.25) and 1.01 g (17%) of cis/trans mixture, respectively, as colorless oils: cis-3-(4-fluorophenoxy)cyclopentanecarbaldehyde; 1H NMR δ9.66 (s, 1H), 7.06-6.90 (m, 2H), 6.86-6.75 (m, 2H), 4.87-4.73 (m, 1H), 2.91-2.73 (m, 1H), 2.40-1.80 (m, 6H): trans-3-(4-fluorophenoxy)cyclopentanecarbaldehyde; 1H NMR δ9.71 (s, 1H), 7.05-6.91 (m, 2H), 6.90-6.75 (m, 2H), 4.87-4.72 (m, 1H), 3.25-3.01 (m, 1H), 2.32-1.79 (m, 6H).

Provenance & Evidence