Imidazole → HCID 59408054, compound

Participants

Reaction Steps

A mixture of tetra(ethylene glycol) 9 (5.00 mL, 28.7 mmol) and imidazole (2.91 g, 42.6 mmol) was dissolved in 10 mL of N,N-dimethylformamide (DMF). TBDPSCl (7.80 mL, 29.4 mmol) was added to the solution dropwise over a 30 min-period using a syringe with an additional amount of DMF (total 20 mL) being added to avoid the reaction mixture becoming cloudy. The reaction was stirred at room temperature for 16 h. DMF was removed under reduced pressure and the crude product was chromatographed (SiO2, gradient, hexane/EtOAc 1:1 to 2:3) to give 6.05 g (14.0 mmol, 49%) of 10 as a light colorless oil. Rf 0.21 (hexane/EtOAc 1:1); 1H NMR (400 MHz, CDCl3) δ 7.68 (m, 4H, H-2 of phenyl), 7.44-7.35 (m, 6H, H-3 and H-4 of phenyl), 3.81 (t, 2H, J=5.5 Hz, CH2OSi), 3.71 (m, 2H, HOCH2CH2), 3.68-3.58 (m, 12H, HOCH2CH2(OCH2CH2)2OCH2CH2), 2.46 (br s, 1H, OH), 1.05 (s, 9H, C(CH3)3); MS (ESI) Calcd for C24H36O5SiNa (M+Na+): 455.2. Found: 455.2.

Provenance & Evidence