Imidazole → (E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol

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Reaction Steps

To a solution of (2E)-2-butene-1,4-diol (8.22 mL, 0.10 mol) and imidazole (8.50 g, 0.125 mol) in DMF (50 mL) at 0° C., was added tert-butyldimethylsilyl chloride (7.50 g, 0.050 mol) in several portions over 10 minutes. The resulting mixture was warmed to room temperature and stirred (2 h), then poured into H2O (200 mL) and extracted with EtOAc (2×150 mL). The organic layer was washed (brine), dried (Na2SO4) and purified by silica gel column chromatography (hexanes:EtOAc) to yield 5 as a colorless oil (9.0 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ 5.60-5.50 (m, 2H), 4.18 (m, 2H), 4.09 (m, 2H), 2.76 (br, 1H), 0.83 (s, 9H), 0.01 (s, 6H). 13C NMR (100 MHz, CDCl3) δ 136.3, 135.4, 64.8, 63.8, 31.1, 23.6.

Provenance & Evidence