Hydrogen Peroxide → HCID 66956821、化合物

関与物質

反応条件

反応手順

A solution of iodine (825 mg, 3.25 mmol) in anhydrous THF (5 mL, then 2×3 mL to rinse) was added dropwise (over 70 min) to a stirred mixture of alkene 166 (5.21 g, 14.4 mmol) and powdered NaBH4 (257 mg, 6.79 mmol) in anhydrous THF (18 mL) at 0° C. under N2. After stirring at 0° C. for 3 h, and then at room temperature for 13 h, the mixture was again cooled to 0° C., treated with 30% H2O2 (6.8 mL) and 3N NaOH (6.8 mL), and then stirred at room temperature for 3 h. Water (160 mL) was then added, and the mixture was extracted with EtOAc (4×160 mL). The extracts were washed with brine (80 mL) and evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-3.5% EtOAc/petroleum ether firstly gave foreruns, and then further elution with 4-8% EtOAc/petroleum ether gave 3-{[tert-butyl(dimethyl)silyl]oxy}-2-{[4-(trifluoromethoxy)phenoxy]methyl}-1-propanol (168) (3.32 g, 61%) as a colourless oil; 1H NMR (CDCl3) δ 7.13 (br d, J=9.0 Hz, 2H), 6.89 (dt, J=9.1, 3.0 Hz, 2H), 4.08 (dd, J=9.3, 6.6 Hz, 1H), 4.04 (dd, J=9.3, 6.0 Hz, 1H), 3.94-3.81 (m, 4H), 2.36 (dd, J=6.1, 5.2 Hz, 1H), 2.19 (m, 1H), 0.89 (s, 9H), 0.07, 0.05 (2 s, 6H); HRFABMS calcd for C17H28F3O4Si m/z [M+H]+ 381.1709. found 381.1707.

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