반응 #85746

반응 방정식

EtOAc Heptane

methyl magnesium bromide

(R,E)-2-methyl-N-(4-(trifluoromethoxy)benzylidene)propane-2-sulfinamide

→

(R)-2-methyl-N—((S)-1-(4-(trifluoromethoxy)phenyl)ethyl)propane-2-sulfinamide

수율 62.0%

용매

Et2O

CH2Cl2

반응 조건

후처리

1. 1
   온도to warm up to room temperature
2. 2
   workup.STIRRINGstirred additional 4 hrs
3. 3
   온도The reaction mixture was cooled again to 0° C.
4. 4
   기타quenched with the slow addition of a saturated NH4Cl solution
5. 5
   workup.ADDITIONThe by-phasic mixture was diluted with DCM and Water
6. 6
   추출the aqueous extracted with DCM two times
7. 7
   세척washed with brine
8. 8
   건조dried (Na2SO4)
9. 9
   여과filtered
10. 10
    농축concentrated to 11.5 g crude white solid

실험 절차

To a solution of (R,E)-2-methyl-N-(4-(trifluoromethoxy)benzylidene)propane-2-sulfinamide (7.7 g, 26.3 mmol) in CH2Cl2 (150 mL), cooled to 0° C. (water/ice bath), under nitrogen, was added 3M methyl magnesium bromide (35 mL, 105 mmol) in Et2O. The reaction mixture was stirred at 0° C. for 30 min, then allowed to warm up to room temperature and stirred additional 4 hrs. The reaction mixture was cooled again to 0° C. and quenched with the slow addition of a saturated NH4Cl solution. The by-phasic mixture was diluted with DCM and Water and the aqueous extracted with DCM two times. The organic phases were combined, washed with brine, dried (Na2SO4), filtered and concentrated to 11.5 g crude white solid. Silica gel column chromatography (EtOAc/Heptane 0 to 30%) afforded (R)-2-methyl-N—((S)-1-(4-(trifluoromethoxy)phenyl)ethyl)propane-2-sulfinamide (5.08 g, 16.2 mmol, 62% yield) as a white crystalline solid. 1H NMR (400 MHz, CDCl3) δ 1.21 (s, 9H) 1.53 (d, J=6.70 Hz, 3H) 3.31 (d, J=2.74 Hz, 1H) 4.59 (qd, J=6.67, 3.37 Hz, 1H) 7.18 (d, J=8.02 Hz, 2H) 7.36 (d, J=8.66 Hz, 2H). LCMS m/z 310.2 (M+H)+, Rt 0.90 min.

출처