Imidazole → 1-[(Tert-butyldimethylsilyl)oxy]but-3-en-2-ol

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To a solution of (+/−)-3-butene-1,2-diol (500 mg, 5.67 mmol) in CH2Cl2 (25 mL) was added imidazole (444 mg, 6.53 mmol). The solution was cooled to 0° C. and t-butyidimethylsilyl chloride (1.0 M in THF, 6.24 mL, 6.24 mmol) was added. The reaction was stirred at 0° C. for 15 minutes and at room temperature for 1 hour and 30 minutes. The mixture was diluted with aqueous NH4Cl and extracted with CH2Cl2 (3×). The organic solution was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography eluting with a solvent gradient (5% EtOAc in hexanes to 100% EtOAc) to provide 827.5 mg of 1-(tert-butyl-dimethyl-silanyloxy)-but-3-en-2-ol. 1H NMR (CDCl3) δ 5.81 (m, 1H), 5.34 (d, 1H), 5.19 (d, 1H), 4.17 (m, 1H), 3.66 (dd, 1H), 3.45 (dd, 1H), 0.90 (s, 9H), 0.08 (s, 6H); MS m/z 202.

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