2,3,4-Trifluorobenzoyl chloride → N-(2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,3,4-trifluoro-N-methylbenzamide

2,3,4-Trifluorobenzoyl chloride (2.32 mL, 18.16 mmol) was added slowly to a stirred mixture of (2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)methylamine (3.44 g, 18.16 mmol) in DCM (200 mL) and 10% aqueous sodium hydroxide solution (200 mL) at 0° C. The reaction was allowed to warm to RT and stirred for a further 24 hours. The phases were separated and the aqueous phase further extracted with DCM (3×100 mL), the combined organics dried (MgSO4), filtered and the solvent removed in vacuo to give a pale yellow oil. The residue was chromatographed on silica, eluting with 0-50% ethyl acetate in isohexane, to give the desired compound as a colourless oil (5.22 g).

1. customThe phases were separated
2. extractionthe aqueous phase further extracted with DCM (3×100 mL)
3. dry with materialthe combined organics dried (MgSO4)
4. filtrationfiltered
5. customthe solvent removed in vacuo
6. customto give a pale yellow oil
7. customThe residue was chromatographed on silica
8. washeluting with 0-50% ethyl acetate in isohexane

ORD record

ord-5a58a21ddba2451fa62ea92ba1d304c8

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943607B2