Imidazole → 2-[2-(t-Butyldimethylsiloxy)ethyl]phenol

Beteiligte Stoffe

Reaktionsschritte

2-Hydroxyethylphenol (XLVa) (15.2 g, 0.11 mol) and t-butyldimethylsilyl chloride (18.2 g, 0.121 mol) were placed together in DMF (120 mL; Aldrich Sure Seal). While the solution was being stirred, imidazole (16.5 g, 0.242 mol) was added portionwise (slightly exothermic). After stirring for 3 h at room temperature, EtOAc (200 mL) was added and the resultant solution was washed with water (3×200 mL) and brine (200 mL). The EtOAc layer was dried over anhydrous sodium sulfate, filtered and concentrated to leave a yellow oil which was purified by silica gel column chromatography (being eluted with 19:1 hexanes/EtOAc) to obtain 27.7 g (0.11 mol, Y: 100%) of the title compound as an oil; Rf: 0.40 (19:1 hexanes/EtOAc); 1H-NMR (CDCl3) δ ppm: 0.067 (6H, s, SiMe2), 0.893(9H, s, SitBu), 2.87 (2H, t, J=5 Hz, ArCH2), 3.91 (2H, t, J=5 Hz, CH2OSi), 6.80 (1H, dt, J=1.3, 7.4 Hz, 5'-H), 6.90 (1H, dd, J=1.2, 8 Hz, 2'-H), 7.00 (1H, dd, J=1,5, 7.3 Hz, 6'-H), 7.12 (1H, dt, J=1.6, 7.5 Hz, 4'-H), 8.29 (1H, s, OH, D2O exchanged); IR (film) 3300 (OH), 1616 cm-1 ; MS (FAB/NOBA) m/e: 253 (MH+), 237, 209.

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