Tributylphosphine → HCID 54199326, compound

Participants

Reaction Steps

To a solution of 3-(2-chlorocyclohept-1-enyl)-2-diazo-3-oxopropionic acid ethyl ester (1 g) in 1,4-dioxan (20 ml) was added a solution of tri-n-butylphosphine (1 ml) in 1,4-dioxan (10 ml). On completion of the addition the reaction mixture was stirred at room temperature for 30 minutes then heated to reflux for 2 h. The solvent was evaporated under reduced pressure and the residue purified by chromatography using a gradient elution: CH2Cl2 (250 ml), CH2Cl2/MeOH 99:1 (250 ml), CH2Cl2/MeOH 98:2 (250 ml), CH2Cl2/MeOH 97:3 (250 ml), CH2Cl2/MeOH 96:4 (250 ml). The appropriate fractions were combined and evaporated under reduced pressure to give a solid (360 mg, 41%). C12H16N2O3 requires C, 61.00; H, 6.83; N, 11.86. Found C, 60.80; H, 6.88; N, 11.84%. δH (250 MHz; CDCl3) 1.42 (3H, t, J=7 Hz, CH3), 1.62 (2H, m, CH2), 1.73 (2H, m, CH2), 1.87 (2H, m, CH2), 2.86 (2H, m, CH2), 3.09 (2H, m, CH2), 4.48 (2H, t, J=7 Hz, CH2), m/z (ESP+) 237 (MH+).

Provenance & Evidence