Potassium Carbonate → HCID 11573667, compound

Participants

Reaction Steps

To a solution of methyl 2,5-dibromopentanoate XIII (22.00 g, 80.3 mmol) and methyl 3-hydroxybenzoate XIV (10.18 g, 66.9 mmol) in DMF (80 mL) was added K2CO3 (12.94 g, 93.7 mmol) at room temperature. The mixture was stirred at room temperature under N2 for 12 hours, then heated at 70° C. for 1 hour. Potassium thioacetate (22.93 g, 200.8 mmol) was added to the mixture, which was heated at 70° C. for 2 hours. The mixture was allowed to cool to room temperature and was diluted with EtOAc (1000 mL). The mixture was washed with H2O (3×300 mL) and brine (2×300 mL). The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography (gradient elution: 10% to 20% EtOAc/hexanes) to afford methyl 3-(4-acetylthio-1-methoxycarbonyl-butoxy)-benzoate XV (8.40 g, 24.7 mmol, 37%) as a yellow oil: Rf 0.26 (hexanes/EtOAc, 4:1): 1H NMR (CDCl3) δ1.73-1.88 (m, 2H), 2.01-2.08 (m, 2H), 2.32 (s, 3H), 2.93 (t, J=7.2 Hz, 2H), 3.75 (s, 3H), 3.89 (s, 3H), 4.69 (t, J=6.2 Hz, 1H), 7.07 (dm, J=8.0 Hz, 1H), 7.33 (t, J=7.9 Hz, 1H) 7.50 (m, 1H), 7.65 (dm, J=7.7 Hz, 1H); 13C NMR (CDCl3) δ25.3, 28.3, 30.5, 31.4, 52.1, 52.2, 75.8, 115.4, 120.0, 122.8, 129.5, 131.4, 157.5, 166.4, 171.3, 195.4.

Provenance & Evidence