Ethyl Acetate → HCID 69627447, compound

Participants

Reaction Steps

To a solution of 2′-hydroxy-3,3″-dimethyl-[1,1′:3′,1″]terphenyl-5′-carboxylic acid (7-phenyl-heptyl)-amide (240 mg, 0.516 mmol) in 2.5 mL anhydrous DMF was added solid K2CO3 (84 mg, 0.613 mmol). The reaction mixture was stirred at room temperature for 2 min before t-butyl bromoacetate (158 mg, 0.812 mmol, 812 μL) was added. The reaction was stirred overnight at room temperature after which point it was diluted with water and extracted with EtOAc (3×). The combined organic layers were washed with water to remove DMF. Then they were dried with Na2SO4 and the solvent was removed in vacuo to give an oil that was subjected to flash column chromatography (15% EtOAc: 85% Hexanes) to yield 180 mg, 60% of a colorless oil. 1H NMR (CDCl3) δ 1.25 (s, 9H); 1.25–1.40 (m, 6H); 1.28–1.47 (m, 4H); 2.40 (s, 6H); 2.57 (t, J=8.18 Hz, 2H); 3.43 (quartet, J=8.18 Hz, 2H); 3.73 (s, 2H); 6.06 (t, J=5.73 Hz, 1H); 7.08–7.20 (m, 5H); 7.20–7.32 (m, 4H); 7.37–7.46 (m, 4H); 7.68 (s, 2H).

Provenance & Evidence