反应详情

温度

-10 °C

A solution of 2-hydroxy-2-difluoromethylpropionic acid (0.9 g, 6.4 mmol) in dry dimethylacetamide (15 ml) was stirred under a nitrogen atmosphere at -10° C. Thionyl chloride (0.76 g, 6.4 mmol) was added and the resulting mixture was allowed to stir at -10° C. for 1 hour. 4-Phenylsulfonylaniline (1.0 g, 4.3 mmol) was then added and the reaction mixture was stirred at -10° C. for a further 15 mins. The solution was then allowed to warm to room temperature where it was stirred overnight. The reaction mixture was poured into ammonium chloride solution and extracted with ethyl acetate. The combined ethyl acetate fractions were washed with water and brine. After drying (Na2SO4) and decolorization (Charcoal) the solution was evaporated in vacuo. A foam was obtained which was triturated with toluene and crystallized from ethyl acetate/hexane to give the title tertiary carbinol (0.72 g, 47%) as white crystals; mp=168°-169° C. 1H-NMR (300 MHz, d6 -DMSO): 1.41 (s, 3H, CH3), 6.13 (t, J=54.9 Hz, 1H, CHF2), 6.76 (s, 1H, OH), 7.58-7.68 (m, 3H, ArH), 7.89-8.01 (m, 6H, ArH), 10.27 (s, 1H, NH). MS (CI, CH4): 356(M+1, 100). Analysis for C16H15F2NO4S: Calculated: C, 54.08; H, 4.25; N, 3.94 Found: C, 53.75; H, 4.40; N, 3.78

1. stirringthe reaction mixture was stirred at -10° C. for a further 15 mins
2. temperatureto warm to room temperature where it
3. stirringwas stirred overnight
4. extractionextracted with ethyl acetate
5. washThe combined ethyl acetate fractions were washed with water and brine
6. dry with materialAfter drying (Na2SO4) and decolorization (Charcoal) the solution
7. customwas evaporated in vacuo
8. customA foam was obtained which
9. customwas triturated with toluene
10. customcrystallized from ethyl acetate/hexane
11. customto give the title tertiary carbinol (0.72 g, 47%) as white crystals