Ethyl diazoacetate → HCID 53959852, compound

Participants

Reaction Steps

To a solution of 2-chlorocyclohept-1-enecarbonyl chloride (4.6 g) and ethyl diazoacetate (2.8 ml) in THF (30 ml) cooled to −70C was added a solution of lithium 2,2,6,6-tetramethylpiperidine (1 equiv.) dropwise. On completion of the addition the reaction mixture was stirred for 1 h. The reaction mixture was quenched by pouring into 1M citric acid (100 ml), then extracted with ether (3×200 ml). The ether extracts were combined, washed with brine, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. The oil was purified by flash chromatography using a gradient elution: hexane/ether (10:1) 500 ml, hexane/ether (9:1) 500 ml, hexane/ether (8:2) 500 ml. The appropriate fractions were combined and evaporated under reduced pressure to give a yellow oil. δH (360 MHz; CDCl3) 1.33 (3H, t, J=7 Hz, CH3), 1.74 (6H, m, CH2), 2.32 (2H, m, CH2), 2.64 (2H, m, CH2), 4.29 (2H, t, J=7 Hz, CH2).

Provenance & Evidence