Water → methyl 2-[(E)-2-phenylvinyl]isonicotinate

HRID 383916ノート

反応式

HRID 383916 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]1(/[CH:18]=[CH:19]/OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:12]1(/[CH:18]=[CH:19]/[C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 22100376[(E)-2-phenylvinyl]boric acid

生成物 1

HCID 59291512methyl 2-[(E)-2-phenylvinyl]isonicotinate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a mixture of methyl 2-chloroisonicotinate, Pd(PPh3)4, and [(E)-2-phenylvinyl]boric acid in dioxane was added a 2 M aqueous Na2CO3 solution, followed by stirring at 90° C. for 5 hours. To the reaction mixture was added water, and the aqueous layer was extracted with EtOAc. The organic layer was dried over MgSO4, and the filtrate was then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc) to obtain methyl 2-[(E)-2-phenylvinyl]isonicotinate as a pale yellow solid.

後処理

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationthe filtrate was then concentrated under reduced pressure
  4. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc)

出典と根拠

ORDレコード
ord-1b46bf55431b4ccda8eb1e1090edfe2f
出典データセット
uspto-grants-2013_02
特許番号
US08367696B2

反応ノート

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