1,2-Epoxybutane → 1-(3-Methoxyphenyl)butan-2-ol

To a stirred suspension of CuI (0.40 g, 2.08 mmol) in 3-methoxyphenylmagnesium bromide in THF (31.2 mL, 1.0M THF solution, 31.2 mmol) at −20° C. was slowly added a solution of 1,2-epoxybutane (1.50 g, 20.8 mmol) in THF (1 mL). The mixture was allowed to warm up to room temperature and stirred at room temperature overnight. The reaction mixture was cooled in an ice bath and quenched with saturated aqueous NH4Cl. The mixture was extracted with ethyl acetate (3×70 mL). The combined organic phase was washed with 1 N NaOH, brine, dried (Na2SO4) filtered, and the filtrate was concentrated to give the crude product as a brown oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (4:1) to give 3.50 g (94%) of compound (51) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.00 (t, J=7.4 Hz, 3H), 1.50-1.65 (m, 2H), 2.62 (dd, J1=13.5 Hz, J2=8.6 Hz, 1H), 2.82 (dd, J1=13.5 Hz, J2=4.1 Hz, 1H), 3.74-3.79 (m, 1H), 3.80 (s, 3H), 6.75-6.85 (m, 3H), 7.20-7.25 (m, 1H).

1. temperatureThe reaction mixture was cooled in an ice bath
2. customquenched with saturated aqueous NH4Cl
3. extractionThe mixture was extracted with ethyl acetate (3×70 mL)
4. washThe combined organic phase was washed with 1 N NaOH, brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customto give the crude product as a brown oil
9. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (4:1)

ORD record

ord-72921622dd57412d84de5fbed3b7e392

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07649093B2