Sodium Carbonate → (E)-3-chloro-5-(prop-1-enyl)picolinonitrile

HRID 1259117노트

반응식

HRID 1259117 반응식
[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](Cl)[CH:7]=1.[CH3:11][C:12]1(C)[C:16](C)(C)OB(/C=C/C)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](/[CH:11]=[CH:12]/[CH3:16])[CH:7]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27696993,5-Dichloro-2-cyanopyridineHCID 113442144,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane

생성물 1

HCID 66893384(E)-3-chloro-5-(prop-1-enyl)picolinonitrile

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 21863594Toluene ethanol용매

실험 절차

A solution of 3,5-dichloropicolinonitrile (1.0 eq.), (E)-4,4,5,5-tetramethyl-2-(prop-1-enyl)-1,3,2-dioxaborolane (1.0 eq.), tetrakis(triphenyl-phosphine)palladium (5 mol %), and 2N aqueous sodium carbonate solution (3.4 eq.) in toluene/ethanol (2:1, 0.04 M) was stirred at 95° C. overnight. After cooling to ambient temperature, the reaction content was diluted with ethyl acetate and water. The two phases were separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vaccuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give a white solid (E)-3-chloro-5-(prop-1-enyl)picolinonitrile.

후처리

  1. customThe two phases were separated
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated en vaccuo
  6. customto obtain a crude residue
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

출처 및 근거

ORD 기록
ord-44d1eee013664488af32069d7a664ac6
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466167B2

반응 노트

불러오는 중…