Sodium Carbonate → 3-Chloro-5-vinylpicolinonitrile

HRID 340224

反応式

HRID 340224 の反応式
[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(C)(C)OB(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]=[CH2:12])[CH:7]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27696993,5-Dichloro-2-cyanopyridineHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 668752253-Chloro-5-vinylpicolinonitrile

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 21863594Toluene ethanol溶媒

実験手順

A solution of 3,5-dichloropicolinonitrile (1.0 eq.), 4,4,5,5-tetramethyl-2-vinyl-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 vacuo. 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.

後処理

  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 vacuo
  6. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)
  7. customto give a white solid

出典と根拠

ORDレコード
ord-aca082d8ee214a8685d1804aabbf4969
出典データセット
uspto-grants-2014_11
特許番号
US08895577B2

関連ノート

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