Imidazole → HCID 68634095, compound

Participants

Reaction Steps

A mixture of 25 (950 mg, 2.34 mmol) and imidazole (396 mg, 5.81 mmol) was dissolved in 5 mL of DMF. TBDPSCl (0.74 mL, 2.79 mmol) was added to the solution dropwise over a 30 min-period using a syringe. The reaction was stirred at room temperature for 16 h. The crude product was chromatographed (SiO2, gradient, hexane/EtOAc 10:1 to 5:1) to give 1.37 g (2.12 mmol, 91%) of 56 which was slightly contaminated with TBDPSCl. Rf 0.46 (hexane/EtOAc 5:1); 1H NMR (400 MHz, CDCl3) δ 7.68 (m, 4H, H-2 of phenyl), 7.43-7.32 (m, 6H, H-3 and H-4 of phenyl), 3.82 (m, 1H, H-3/H-7), 3.67 (s, 3H, CO2CH3), 3.46 (m, 1H, H-3/H-7), 2.40-0.69 (m, 28H), 1.04 (s, 9H, C(CH3)3), 0.93 (d, 3H, J=6.4 Hz, CH3), 0.79 (s, 3H, CH3), 0.64 (s, 3H, CH3); MS (ESI) Calcd for C41H60O4SiNa (M+Na+): 667.4. Found: 667.4.

Provenance & Evidence