Water → (NZ)-4-methyl-N-[4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butylidene]benzenesulfinamide

Temperature

0 °C

To the crude organic extract of 4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butyraldehyde (prepared as in Example 26, part F, 0.6 g, 2.88 mmol) in ether (5 mL) was added titanium (IV) ethoxide (2.63 g, 11.54 mmol) followed by (S)-(+)-toluene sulfinamide (0.537 g, 3.46 mmol) and the solution was heated to reflux for 5 h. The mixture was then cooled to 0° C. and water (35 mL) was added to precipitate titanium salts. The suspension was filtered through a pad of the Celite® reagent and the filter cake was washed with CH2Cl2. The layers of the filtrate were separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered, and concentrated to obtain a crude yellow oil (1.05 g). The crude product was purified by the Biotage Flash™ 40 chromatography system, eluent: 1:9 EtOAc-hexanes, to afford 4-methyl-N-[(1Z)-4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butylidene]benzenesulfinamide as a yellow oil (0.41 g, 41.2%). Mass Spectrum (−ESI): 344 (M−H)−.

1. temperaturethe solution was heated
2. temperatureto reflux for 5 h
3. customto precipitate titanium salts
4. filtrationThe suspension was filtered through a pad of the Celite® reagent
5. washthe filter cake was washed with CH2Cl2
6. customThe layers of the filtrate were separated
7. extractionthe aqueous layer was extracted with CH2Cl2
8. dry with materialThe combined organic extracts were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto obtain a crude yellow oil (1.05 g)
12. customThe crude product was purified by the Biotage Flash™ 40 chromatography system, eluent

ORD record

ord-50a50324019c40929f51c2373534c833

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858658B2