Water → Ethyl 6-phenylnicotinate

HRID 914455

反応式

HRID 914455 の反応式
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](Cl)=[N:7][CH:6]=1)[CH3:2].[C:13]1(OB(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][CH:6]=1)[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 2799611Ethyl 6-chloronicotinate

生成物 1

HCID 11096332Ethyl 6-phenylnicotinate収率 86.8%

試薬・触媒・溶媒 2

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

実験手順

Under nitrogen atmosphere, 6-chloronicotinic acid ethyl ester (24.0 g) and phenylboric acid (23.6 g) were dissolved in dioxane (200 mL) and aqueous sodium carbonate solution (2M, 100 mL), tetrakis(triphenylphosphine)palladium (7.0 g) was added, and the mixture was refluxed for 8 hr. The reaction mixture was cooled, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=7:1 to 5:1) to give the title compound (25.5 g) as a white solid.

後処理

  1. temperaturethe mixture was refluxed for 8 hr
  2. temperatureThe reaction mixture was cooled
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=7:1 to 5:1)

出典と根拠

ORDレコード
ord-ad7507a1bf0f4abaa0616efbe73537fc
出典データセット
uspto-grants-2011_09
特許番号
US08026370B2

関連ノート

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