Hydrogen Peroxide → 3-{[Tert-butyl(dimethyl)silyl]oxy}-2-[(4-iodophenoxy)methyl]-1-propanol

Participants

Reaction Conditions

Reaction Steps

A solution of iodine (282 mg, 1.11 mmol) in anhydrous THF (1.5 mL, then 2×0.75 mL to rinse) was added dropwise (over 40 min) to a stirred mixture of alkene 167 (1.71 g, 4.23 mmol) and powdered NaBH4 (90 mg, 2.38 mmol) in anhydrous THF (5.5 mL) at 0° C. under N2. After stirring at 0° C. for 4 h, and then at room temperature for 13 h, the mixture was again cooled to 0° C., treated with 30% H2O2 (2.4 mL) and 3N NaOH (2.4 mL), and then stirred at room temperature for 3 h. Water (50 mL) was then added, and the mixture was extracted with EtOAc (4×50 mL). The extracts were washed with brine (50 mL) and evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-2% EtOAc/petroleum ether firstly gave foreruns, and then further elution with 4-5% EtOAc/petroleum ether gave 3-{[tert-butyl(dimethyl)silyl]oxy}-2-[(4-iodophenoxy)methyl]-1-propanol (169) (1.26 g, 71%) as a pale yellow oil; 1H NMR (CDCl3) δ 7.55 (dt, J=9.0, 2.7 Hz, 2H), 6.69 (dt, J=9.0, 2.7 Hz, 2H), 4.06 (dd, J=9.3, 6.7 Hz, 1H), 4.01 (dd, J=9.3, 5.9 Hz, 1H), 3.93-3.80 (m, 4H), 2.36 (dd, J=6.3, 5.1 Hz, 1H), 2.17 (sept, J=5.4 Hz, 1H), 0.89 (s, 9H), 0.06, 0.05 (2 s, 6H); HRFABMS calcd for C16H28IO3Si m/z [M+H]+ 423.0853. found 423.0849.

Provenance & Evidence