Dimethylformamide → HCID 59314121, compound

Participants

Reaction Steps

A 100 mL round bottom flask containing the 2-(hydroxy-3-methyl-benzoyl)-indan-2-carboxylic acid ethyl ester (0.62 g, 1.87 mmol) is charged with DMF (3 mL) and a stirring bar is added. After dissolution of the starting material, the K2SO4 (0.791 g, 5.95 mmol) is added followed by a solution of 1-bromo-2-butyne (537 μL, 5.95 mmol). After stirring for 110 h tlc analysis (silica, 1:1 EtOAc/heptanes) indicates that the starting material is consumed. The material is cleanly converted to a UV positive spot with a slightly lower Rf. The reaction is diluted with EtOAc (80 mL) and filtered through a pad of Celite. The filtrate is transferred to a separatory funnel. This is washed repeatedly with a saturated aqueous solution of NaHCO3 (2×50 mL) and brine (50 mL), dried over MgSO4, filtered and evaporated in vacuo to yield 0.75 g of a light brown oil. This is purified (silica, 40 g ISCO column 10% EtOAc in heptanes for 3 column volumes followed by a linear gradient to 50% EtOAc in heptanes for 10 column volumes). 17 mL fractions of UV positive eluent are collected. Fractions 2 through 8 are combined, evaporated in vacuo and pumped dry to yield 0.79 g of a white solid.

Provenance & Evidence