HCID 89670264, compound → HCID 89653854, compound

Participants

Reaction Steps

A solution of 65a (5.5 g, 0.016 mol) in AcOH (50 mL) was heated at 100° C. for 1 hr. The reaction mixture was then concentrated in vacuo. The residue was dissolved in CH2Cl2 (100 mL), washed with saturated NaHCO3 (2×75 mL) and brine (75 mL), filtered through phase separation filter paper, and concentrated in vacuo to give a solid. The solid was triturated with EtOAc (35 mL), collected, and dried to give 3.7 g (71%) of 66a. HPLC analysis showed a purity of 80%. The solid was chromatographed on 75 g silica gel with 25 g of anhydrous sodium sulfate on top packed with hexanes. The column was eluted with 50 mL portions of 10% EtOAc in hexanes for fractions 1-4, 25% EtOAc in hexanes for fractions 5-8, and 50% EtOAc in hexanes for fractions 9-28. The pure product was eluted in fractions 15-20 (HPLC analysis) to give 3.2 g (61%) of 66a as a white solid. HPLC analysis showed a purity of 97%. 1H NMR (60 MHz, CDCl3): δ 7.7 (d, 1H), 7.4-6.4 (m, 6H), 6.8 (br s, 1H), 5.0 (s, 2H), 4.1 (d, 2H), 3.7 (s, 3H), 2.5-1.6 (m, 1H), 1.0 (d, 6H) ppm.

Provenance & Evidence