Nitrogen → 3,N,N-Trimethyl-4-vinylbenzamide

HRID 1754903노트

반응식

HRID 1754903 반응식
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:13].[CH:14]([B-](F)(F)F)=[CH2:15].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].N#N>C1COCC1.Cl[Pd]Cl.O>[CH3:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[CH:14]=[CH2:15])[C:6]([N:8]([CH3:10])[CH3:9])=[O:7]

참가 물질

9

반응물 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 189605694-bromo-N,N,3-trimethylbenzamideHCID 23679353Potassium vinyltrifluoroborate

생성물 1

HCID 668162113,N,N-Trimethyl-4-vinylbenzamide수율 90.5%

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 4-bromo-3,N,N-trimethyl-benzamide (798 mg, 3.30 mmol), potassium vinyltrifluoroborate (579 mg, 4.32 mmol), PdCl2 (59.0 mg, 0.333 mmol), PPh3 (265 mg, 1.01 mmol) and Cs2CO3 (3.22 g, 9.90 mmol) in THF (6.5 ml)-H2O (0.65 ml) was heated with stirring at 85° C. for 21 hours in a sealed test tube in an N2 atmosphere. The reaction mixture was cooled to room temperature and then extracted with ether. The organic layer was washed with water, and then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give 3,N,N-trimethyl-4-vinyl-benzamide (565 mg, 90%).

후처리

  1. temperaturewas heated
  2. extractionextracted with ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-b0aa6487ebc643aaa7139fa225f38a9b
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169254B2

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