Diethyl Ether → HCID 59225756, compound

To a magnetically stirred solution of methyl Grignard (19.9 mL of a 3 M solution in ether (Et2O), 59.7 mmol) in Et2O (167 mL) was added a solution of 2-trifluoromethylpyrimidine-5-carbaldehyde (9.56 g, 54.3 mmol) in Et2O (50 mL) at 0° C., and the resulting pale yellow solution was warmed to room temperature (RT) and stirred for 2.5 h. The reaction was quenched by the addition of saturated aqueous ammonium chloride (NH4Cl) (50 mL) at 0° C., and the mixture was warmed to RT. The phases were separated and the organic phase was dried over Na2SO4, filtered, and concentrated to give a light yellow oil (9.32 g crude). The oil was purified by flash chromatography (330 g SiO2, 0→100% EtOAc/hexanes gradient) to give 1-(2-trifluoromethylpyrimidin-5-yl)ethanol (E) (8.87 g, 85%) as a light yellow solid: mp 43-45° C.; 1H NMR (300 MHz, CDCl3) δ 8.92 (s, 2H), 5.15-5.07 (m, 1H), 2.26 (d, J=4.0 Hz, 1H), 1.62 (d, J=6.5 Hz, 3H); MS (EI) m/z 192 (M)+.

1. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride (NH4Cl) (50 mL) at 0° C.
2. temperaturethe mixture was warmed to RT
3. customThe phases were separated
4. dry with materialthe organic phase was dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a light yellow oil (9.32 g crude)
8. customThe oil was purified by flash chromatography (330 g SiO2, 0→100% EtOAc/hexanes gradient)

ORD record

ord-d10d75fba7e94ec6ad02847423f88032

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324209B2