Styrene → 2-Styrylnicotinic acid methyl ester

HRID 1072532노트

반응식

HRID 1072532 반응식
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1Cl.[CH2:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 7501StyreneHCID 11776TriphenylphosphineHCID 517045Sodium AcetateHCID 819931Methyl 2-chloronicotinate

생성물 1

HCID 536734442-Styrylnicotinic acid methyl ester수율 82.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of the ester 18 (48.8 g, 0.28 mol) in DMF (450 mL) was added styrene (165 mL, 1.42 mol), palladium acetate (6.5 g, 30 mmol), sodium acetate (47 g, 0.57 mol) and triphenyl phosphine (30 g, 0.11 mol). The mixture was heated under reflux for 22 h. The palladium-catalyst was removed by filtration through a Celite pad. The filtrate was concentrated under reduced pressure, and the residue was dissolved in a minimum amount of ethyl acetate. To the above solution was added hexane. After removal of the precipitate by filtration, the filtrate was concentrated. The resulting crude material was purified by FCC (1:1 v/v ethyl acetate-hexane) to afford the ester 19 (55.0 g, 81%) as a light yellow oil:

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 22 h
  3. customThe palladium-catalyst was removed by filtration through a Celite pad
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in a minimum amount of ethyl acetate
  6. additionTo the above solution was added hexane
  7. customAfter removal of the precipitate
  8. filtrationby filtration
  9. concentrationthe filtrate was concentrated
  10. customThe resulting crude material was purified by FCC (1:1 v/v ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-48ac55c99acf48f3bf5d22ec1696c44f
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911460B2

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