Imidazole → (2R)-1-(benzyloxy)-3-[(triisopropylsilyl)oxy]-2-propanol

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Reaction Steps

Chloro(triisopropyl)silane (12.2 mL, 0.057 mol) was added dropwise at 20° C. to a stirred solution of diol 78 (9.52 g, 0.052 mol) and imidazole (5.33 g, 0.078 mol) in DMF (150 mL) and stirring was continued for 16 h. Most of the DMF was removed under reduced pressure and the residue was partitioned between EtOAc and water. The organic extract was washed well with water, then brine, and was evaporated to give an oil, which was chromatographed on silica. Elution with petroleum ether gave fore fractions, and then further elution with EtOAc/petroleum ether (1:19) gave (2R)-1-(benzyloxy)-3-[(triisopropylsilyl)oxy]-2-propanol (79) (13.80 g, 78%) as a colourless oil: [α]19 −0.78° (c, 8.93, CHCl3); 1H NMR (CDCl3) δ 7.41-7.27 (m, 5H), 4.55 (s, 2H), 3.90-3.84 (m, 1H), 3.79-3.72 (m, 2H), 3.59-3.51 (m, 2H), 2.52 (d, J=5.1 Hz, 1H), 1.13-1.03 (m, 21H). APCI MS m/z 339 [M+H]+.

Provenance & Evidence