Cesium carbonate → 3-[5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-2-nitro-phenyl]-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile

HRID 658062노트

반응식

HRID 658062 반응식
F[C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-:21])=[O:20])=[C:6]([CH:8]=[C:9]([CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:10]#[N:11])[CH:7]=1.[O:22]1[CH2:27][CH2:26][CH2:25][O:24][CH:23]1[C:28]1[CH:29]=[C:30]([SH:34])[CH:31]=[CH:32][CH:33]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[O:22]1[CH2:27][CH2:26][CH2:25][O:24][CH:23]1[C:28]1[CH:29]=[C:30]([S:34][C:2]2[CH:3]=[CH:4][C:5]([N+:19]([O-:21])=[O:20])=[C:6]([CH:8]=[C:9]([CH2:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:10]#[N:11])[CH:7]=2)[CH:31]=[CH:32][CH:33]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 578640833-[1,3]Dioxan-2-yl-benzenethiolHCID 689786393-(5-Fluoro-2-nitro-phenyl)-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile

생성물 1

HCID 687376013-[5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-2-nitro-phenyl]-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3-(5-Fluoro-2-nitro-phenyl)-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile (1.2 g, 4.07 mmol) and 3-[1,3]dioxan-2-yl-benzenethiol (0.8 g, 4.07 mmol) were added to a mixture of Cs2CO3 (2.78 g, 8.56 mmol) in DMF (100 mL). The resulting mixture was stirred at room temperature overnight, then diluted with ethyl acetate and washed with H2O. The organic phase was separated, dried with MgSO4, and filtered. The solvent was removed to yield an oil, which was purified by silica column chromatography (40% EtOAc/heptane) to yield an oil.

후처리

  1. washwashed with H2O
  2. customThe organic phase was separated
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed
  6. customto yield an oil, which
  7. customwas purified by silica column chromatography (40% EtOAc/heptane)
  8. customto yield an oil

출처 및 근거

ORD 기록
ord-0e7736d15a2a4212ac8062ae85e49530
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076358B2

반응 노트

불러오는 중…