Methyl iodide → HCID 59371269, compound

To a solution of 1-(3-bromophenyl)-3-phenyl-2(R)-propanol (437 mg, 1.50 mmol) in 20 mL of anhydrous THF was added NaH (70% dispersion in mineral oil, 64 mg, 1.87 mmol, 1.24 equiv.) at 0° C. under N2. The mixture was warmed to room temperature and stirred for 30 min, then CH3I (2.1 g, 15 mmol, 10 equiv.) was added at room temperature. The mixture was stirred for 3 h at room temperature. The reaction was quenched with saturated aqueous NH4Cl solution, and the mixture was extracted with EtOAc (3×50 mL). The combined organic phases were washed with brine and dried over Na2SO4. After filtration and concentration, the residue was purified by CC on silica gel with EtOAc/petroleum ether 1:20 to provide the methyl ether (347 mg, 76%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 7.36-7.12 (m, 9H), 3.61 (quintet, 1H, J=6.3 Hz), 3.27 (s, 3H), 2.85 (dd, 1H, J=13.8, 6.6 Hz), 2.75 (dd, 3H, J=12.9, 6.6 Hz).

1. stirringThe mixture was stirred for 3 h at room temperature
2. customThe reaction was quenched with saturated aqueous NH4Cl solution
3. extractionthe mixture was extracted with EtOAc (3×50 mL)
4. washThe combined organic phases were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationAfter filtration and concentration
7. customthe residue was purified by CC on silica gel with EtOAc/petroleum ether 1:20

ORD record

ord-764f087b9cbf455691b119dd328ce219

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445684B2