2,2,2-Trifluoroethanol → HCID 21478866, compound

Temperature

0 °C

A solution of 2,2,2-trifluoroethanol (2.61 g, 26.10 mmol) in tetrahydrofuran (12 ml) was added dropwise to a suspension of sodium hydride (1.31 g, 32.60 mmol) in tetrahydrofuran (48 ml) at 0° C. The mixture was stirred at 0° C. for 30 min and a solution of 4,6-dichloropyrimidine (3.6 g, 24.16 mmol) in tetrahydrofuran (12 ml) was added at 0° C. The reaction mixture was stirred at ambient temperature for 3 h and poured into sat. aqueous ammonium chloride and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The orange residue was purified by column chromatography (10-40% ethyl acetate/hexanes) to afford 4-chloro-6-(2,2,2-trifluoroethoxy)pyrimidine (2.0 g, 2.41 mmol, 38.9% yield) as a pale yellow oil. MS (LC/MS) R.T.=2.78; [M+H]+=213.12.

1. stirringThe reaction mixture was stirred at ambient temperature for 3 h
2. extractionextracted with ethyl acetate
3. extractionThe ethyl acetate extract
4. washwas washed with water
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customThe orange residue was purified by column chromatography (10-40% ethyl acetate/hexanes)

ORD record

ord-518abffe2f2a467aad300fdf243de47d

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309577B2