Potassium Carbonate → 4-Methyl-2-phenylquinoline

HRID 2308153노트

반응식

HRID 2308153 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 209194-Methyl-2-phenylquinoline수율 61%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e2cf8114536042a0951a2f81f871b771
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06835469B2

반응 노트

불러오는 중…