Imidazole → 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)isobenzofuran-1(3H)-one

Participants

Reaction Steps

3-(2-hydroxyethyl)-3H-isobenzofuran-1-one (1.03 g, 5.781 mmol) dissolved in THF (10 mL) under N2 and TBDMSCl (958.4 mg, 6.359 mmol) then imidazole (472.3 mg, 6.937 mmol) added at RT. Reaction mixture stirred overnight then concentrated. Residue partitioned between EtOAc and water. Aqueous phase extracted with EtOAc and combined organics dried and concentrated. Residue purified by chromatography (silica, 0-100% EtOAc-petrol gradient elution). Title compound obtained as a colourless oil (1.47 g, 87%), 1H NMR (400 MHz, DMSO) 0.00 (3H, s), 0.01 (3H, s), 0.83 (9H, s), 1.76-1.85 (1H, m), 2.23-2.31 (1H, s), 3.71-3.80 (2H, m), 5.66 (1H, dd), 7.57 (1H, t), 7.68 (1H, d), 7.75 (1H, dt), 7.81 (1H, d); MS (ES+) 293.0.

Provenance & Evidence