Diethyl Oxalate → HCID 57443248, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5 mg per mL Rieke® magnesium in THF (37.9 mmol, 40 mL) at room temperature is added bromomethyl cyclobutane (37.9 mmol, 4.25 mL) dropwise. After the addition, the reaction is heated to 60° C. for 1 h. The mixture is transferred via syringe to a −78° C. solution of diethyl oxalate (37.9 mmol, 5.14 g) in THF (20 mL). The reaction is allowed to warm to 0° C. and is quenched with 1N HCl. Diethyl ether is added (20 mL) and the layers are separated. The organic layer is dried (Na2SO4) and adsorbed onto silica and purified using a gradient to 0-10% EtOAc/Hexanes to yield the title compound (2.3 g, 37%). LC-MS: 171.0 (M+1).

Provenance & Evidence