Potassium Carbonate → HCID 131734194, compound

Participants

Reaction Steps

A similar procedure (Hursthouse, M. B.; Khan, A.; Marson, C. M.; Porter, R. A. Tetrahedron Lett. 1995, 36, 33, 5979-5982) to that described for the preparation of 207 was followed using NRB (0.37 g, 0.7 mmol) and potassium carbonate (0.25 g, 1.8 mmol) in dimethylformamide (5 mL), and octyl chloroacetate (0.32 g, 1.5 mmol) in dimethylformamide (2 mL), and the mixture stirred at room temperature for 2 h. Purification by flash chromatography (hexane/ethyl acetate 2:1) afforded 369 as a white solid (0.34 g, 0.5 mmol, 71%). 1H NMR (400 MHz, CDCl3) δ 0.87-0.90 (3H, m, O(CH2)7CH3), 1.26-1.30 (10H, m, OCH2CH2(CH2)5CH3), 1.61-1.63 (2H, m, OCH2CH2(CH2)5CH3), 3.40-4.56 (8H, m, OCH2(CH2)6CH3, NCH2, H-1, H-2, H-3, H-4), 5.48 (0.5H, s, OH), 5.52 (0.3H, m, V/H-6), 5.53 (0.5H, s, OH), 5.55 (0.4H, m, Y/H-6), 6.02 (0.1H, m, U/H-6), 6.04 (0.2H, m, W/H-6), 6.70-7.60 (16H, m, Ar), 8.40-8.60 (2H, m, αPyr).

Provenance & Evidence