Potassium Carbonate → 4-Methyl-2-phenylquinoline

HRID 2308153ノート

反応式

HRID 2308153 の反応式
Cl[C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.COCCOC>[C:13]1([C:2]2[CH:11]=[C:10]([CH3:12])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 694492-Chloro-4-methylquinoline

生成物 1

HCID 209194-Methyl-2-phenylquinoline収率 61%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-Chloro-4-methylquinoline (5.0 g, 30 mmol) and phenyl boronic acid (4.4 g, 36 mmol) were dissolved into 100 mL of ethylene glycol dimethyl ether. To the stirred reaction was added triphenylphosphine (0.8 g) and palladium(II) acetate, followed by 50 mL of a 2 M solution of potassium carbonate. The reaction was refluxed for 16 hours. After cooling, the aqueous layer was discarded and additional ethyl acetate added. The organics were washed with a saturated solution of sodium chloride and separated. The organic layer was dried over magnesium sulfate, concentrated, and purified on a silica gel column using 20% ethyl acetate and hexanes as the eluants. The pure fractions were combined and concentrated to give 2-phenyl-4-methylquinoline (4.0 g, 61% yield) as an oil.

後処理

  1. customTo the stirred reaction
  2. temperatureThe reaction was refluxed for 16 hours
  3. temperatureAfter cooling
  4. washThe organics were washed with a saturated solution of sodium chloride
  5. customseparated
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated
  8. custompurified on a silica gel column
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-e2cf8114536042a0951a2f81f871b771
出典データセット
uspto-grants-2004_12
特許番号
US06835469B2

反応ノート

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