反应详情

A solution of NaClO2 (1.55 g, 17 mmol) and NaH2PO4 H2O (1.42 g, 10.3 mmol) in H2O was added to a mixture of 4-chloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carbaldehyde (694 mg, 1.7 mmol), 2-methyl-2-butene (10.8 mL, 21.5 mmol, 2 M in THF), and tBuOH (1.33 mL) in THF (5.5 mL) at room temperature. The mixture was stirred overnight and separated and the aqueous layer was extracted with EtOAc. The combined extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography (0-80% 0.1%) formic acid solution of EtOAc in DCM) to give the title compound (740 mg, >99%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.83 (2H, s) 4.80 (2H, s) 3.56 (2H, t, J=8.1 Hz) 0.83-0.91 (11H, m) 0.08 (6H, s) −0.04 (9H, s). LCMS: m/z 421 (M+1).

1. customseparated
2. extractionthe aqueous layer was extracted with EtOAc
3. dry with materialThe combined extracts were dried over sodium sulfate
4. concentrationconcentrated
5. customThe residue was purified by column chromatography (0-80% 0.1%) formic acid solution of EtOAc in DCM)