Toluene → HCID 21094005, compound

Participants

Reaction Conditions

Reaction Steps

DMPU (50 mL, 413 mmol) was added to a solution of LDA (65 mL of a 1.8M solution in n-C7H16-THF-PhEt, 117 mmol) in anhydrous THF (250 mL) at −78° C. The mixture was stirred for 1 h to generate a cream precipitate. A solution of (4-methanesulfonylphenyl)acetic acid (12.00 g, 56 mmol) in anhydrous THF (120 mL) was added over 20 min. More anhydrous THF (30 mL) was added, then the thick yellow slurry was stirred for 1 h. The mixture was treated with a solution of 2-chloromethylthiophene (7.50 g, 57 mmol) and PhMe (5.20 g, 57 mmol) in anhydrous THF (20 mL), then stirring was continued at −78° C. for 20 min. The reaction mixture was then allowed to warm to 20° C. over 16 h, before being quenched with H2O (500 mL). The THF was removed under reduced pressure, then 12M HCl was added to adjust the pH to 2. The mixture was extracted with EtOAc (2×300 mL), then the extracts were washed with H2O (2×200 mL) and brine (2×100 mL), before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (IH-EtOAc, 3:2 containing 0.5% AcOH) furnished the title compound: m/z (ES+)=638.3 [2M+NH4]+.

Provenance & Evidence