Hydrogen Peroxide → HCID 58052452, compound

Participants

Reaction Steps

BH3.THF (1 M in THF, 16.5 ml, 1.1 eq.) was added dropwise to a stirred solution of 2-methyl-2-butene (1.75 ml, 1.1 eq.) in dry THF (15 ml) at 0° C. An hour later, a cold solution of ethyl 2-(2-methoxyethyl)-2-methylpent-4-enoate (3.00 g, 1 eq.) in THF (15 ml) was rapidly added. After the reaction mixture had been stirred at room temperature for 1 h, it was quenched with MeOH at 0° C., and then buffer (pH 7, 0.5 M phosphate solution, 18 ml) and H2O2 (30% in water, 18.4 ml, 12 eq.) were added. The reaction mixture was stirred at room temperature for 14 h, poured into brine and extracted with ether. The combined organic phase was washed with saturated aqueous Na2S2O3 solution, water and brine, dried over Na2SO4, and concentrated. Silica gel chromatography using 5-50% ether-DCM yields the title compound (3.27 g, 39%).

Provenance & Evidence