Sodium Carbonate → HCID 67517443, compound

Participants

Reaction Steps

To a solution of [3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]acetic acid (0.75 g, 2.7 mmol) in DCM (25 mL) was added oxalyl chloride (0.28 mL, 3.2 mmol) and a drop of DMF. The mixture was allowed to stir at RT until all solids disappeared. At that point, the solution was cooled to to 0° C. with an ice bath, and aluminum chloride (1.1 g, 8.0 mmol) was added into the reaction slowly. After stirring the mixture for another 10 minutes, ethylene was bubbled through the reaction via a long needle. TLC showed complete reaction within 30 minutes. The reaction was poured into ice water, neutralized with sodium carbonate, extracted with DCM, dried, concentrated, and purified by MPLC (Hexane/EtOAc). LC-MS (IE, m/z): 292 [M+1]+.

Provenance & Evidence