Hydrogen Peroxide → HCID 58052452, compound

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%).

1. customit was quenched with MeOH at 0° C.
2. stirringThe reaction mixture was stirred at room temperature for 14 h
3. extractionextracted with ether
4. washThe combined organic phase was washed with saturated aqueous Na2S2O3 solution, water and brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated

ORD record

ord-c8a3b668991c40f9ae1d318bb4f6e6ab

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324239B2