Succinic anhydride → HCID 10101221, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (9) (2.2 g, 3.48 mmol), succinic anhydride (0.55 g, 5.5 mmol) and pyridine (70 mL) was heated at 81° C. for 2 hours. Solvent was removed in vacuo and cold 1N HCl (100 mL) was added. Extraction was carried out with CHCl3 (6×75 mL), followed by a water wash (100 mL). Solvent removal and flash column chromatography, eluting with 7% MeOH/CH2Cl2, afforded 1.98 g (81%) of (10) as an oil: 300 MHz NMR δ 1.2-1.7 (m+s, 21 H), 2.53 (t, 2 H, J=7), 2.67 (s, 4 H), 2.78-2.86 (m, 2 H), 3.02-3.11 (m, 2 H), 3.22 (q, 2 H, J=6), 3.56-3.77 (m, 4 H), 4.7 (br s, 1 H), 4.83 (s, 2 H), 4.86 (s, 2 H) , 6.73 (br s, 1 H) , 7.38 (s, 10 H) . Anal. calcd. for C37H54N4O9 : C, 63.59; H, 7.79; N, 8.02. Found: C, 63.4 5; H, 7.81; N, 8.07.

Provenance & Evidence