반응 #73540

ord-4e96f7796f8746948ad806fa4b810484

반응 방정식

C=CCN(c1ccccc1)S(=O)(=O)c1ccc(Cl)nc1
6-chloro-N-phenyl-N-(prop-2-en-1-yl)pyridine-3-sulfonamide
C1CCOC1.CCCCCC
mixture ( 1/1 )
C1CCOC1.CCCCCC
n-hexane THF
C[N+]1([O-])CCOCC1
NMO
O=S(=O)(c1ccc(Cl)nc1)N(CC(O)CO)c1ccccc1
6-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide
수율 80.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    추출extracted with Et2O (2×100 mL)
  2. 2
    건조dried over Na2SO4
  3. 3
    여과filtered
  4. 4
    농축concentrated under reduced pressure

실험 절차

To a solution of 1.3 g (4.2 mmol) of 6-chloro-N-phenyl-N-(prop-2-en-1-yl)pyridine-3-sulfonamide in 17 mL of a mixture (1/1) of tBuOH and water are added, at room temperature, 1.37 g (11.7 mmol) of NMO and 0.52 mL (0.04 mmol) of 2.5% OsO4 in tBuOH. Stirring is continued for 12 hours. The medium is then diluted with 200 mL of water and extracted with Et2O (2×100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. 1.14 g of 6-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide are obtained in the form of an oil, which is used without further purification in the following step.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08541455B2uspto-grants-2013_09