[CH2:1]([O:4][C:5]([CH3:9])([CH3:8])[CH2:6][OH:7])[CH:2]=[CH2:3].C1C=C(Cl)C=C(C(OO)=[O:18])C=1.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH3:8][C:5]([O:4][CH2:1][CH:2]1[CH2:3][O:18]1)([CH3:9])[CH2:6][OH:7]
2-(allyloxy)-2-methylpropan-1-ol (2.37 g, 18.2 mmol) was dissolved in DCM (70 mL) and cooled to 0° C. mCPBA (77% max, 15.71 g) was added. The suspension was stirred at 0° C. for 6.5 hr before saturated NaHCO3 solution and Na2S2O3 solution were added. It was stirred at 0° C. for 15 min and the two layers were separated. The aqueous layer was extracted twice with DCM. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting residue was purified on a silica gel column (heptane:EtOAc 1:0 to 1:2) to give the product as a colorless oil (910 mg, 34%). 1H NMR (400 MHz, CDCl3) δ ppm 3.65 (1H, dd, J= 11.2, 2.8 Hz), 3.47 (1H, br s), 3.31-3.41 (3H, m), 3.07-3.09 (1H, m), 2.74 (1H, t, J= 4.8 Hz), 2.63-2.65 (1H, m), 1.12 (6H, s).
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