2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 58635311, compound

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Reaction Steps

To a solution of {[(2R)-2-azido-4-(4-methoxyphenoxy)butyl]oxy}(tert-butyl)dimethylsilane (4.7 g, 12.86 mmol) in 19:1 DCM/water at 0° C. was added DDQ (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone) (3.5 g, 15.43 mmol, 1.2 eq) and the mixture was stirred (from 0° C. to rt) until all starting material disappeared as indicated by TLC (thin layer chromatography) analysis. Most DCM was then removed in vacuo and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with water and saturated NaHCO3 repeatedly until a pale yellow organic solution was obtained. The organic solution was dried and the crude was purified by silica gel chromatography (5% acetone/toluene) to give the desired product (3R)-3-azido-4-{[tert-butyl(dimethyl)silyl]oxy}butan-1-ol. 1H NMR (400 MHz, Acetone-d6): δ3.89 (1 H, dd), 3.73-3.65 (5 H, m), 1.76-1.68 (1 H, m), 1.62-1.54 (1 H, m), 0.94 (9 H, s), 0.13 (6 H, s).

Provenance & Evidence