Acetic Acid → HCID 18317253, compound

Participants

Reaction Steps

Under Ar, a solution of 25 (4.0 g, 12.8 mmol) in DMSO (30 mL) was treated with 95% NaH (0.35 g, 13.8 mmol). After stirring at room temperature for 15 min, a solution of 5 (3.9 g, 13.2 mmol) in DMSO (20 mL) was added in one portion to the deep red solution. After stirring at room temperature for 18 h, 2N AcOH was added and then poured carefully in saturated Na2CO3. The basic aqueous solution was extracted with EtOAc (3×). The organic extracts were backwashed with H2O, brine, dried, filtered and concentrated to dryness. The residue was chromatographed on a Still column (80 mm) and the product was eluted with 30% EtOAc-hexanes to yield 1.5 g of 26.

Provenance & Evidence