Water → 4-{4-[4-(3-Cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile

HRID 48136

반응식

HRID 48136 반응식
F[B-](F)(F)F.[CH2:6]([C:15]1[CH:20]=[CH:19][C:18]([N+]#N)=[CH:17][CH:16]=1)[C:7]1[CH:12]=[CH:11][C:10]([N+]#N)=[CH:9][CH:8]=1.F[B-](F)(F)F.[CH2:28]([C:31]#[N:32])[CH:29]=[CH2:30].O>C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:31]([CH2:28][CH:29]=[CH:30][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:15]2[CH:20]=[CH:19][C:18]([CH:30]=[CH:29][CH2:28][C:31]#[N:32])=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)#[N:32]

참가 물질

6

반응물 3

HCID 962WaterHCID 80093-ButenenitrileHCID 117320104,4'-Methylenebisbenzenediazonium bis(tetrafluoroborate)

생성물 1

HCID 570915964-{4-[4-(3-Cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile수율 61%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 702Ethanol용매

반응 조건

온도
40 °C

실험 절차

A suspension of 4,4′-methanediyl-bis-benzenediazonium tetrafluoroborate (11.9 g, 0.03 mol), prepared according to the method of example 6.1, allyl cyanide (8.05 g; 0.12 mol), and palladium acetate (0.135 g, 0.6 mmol) in 80 ml of ethanol is heated at 40° C. during 22 h. The heterogeneous reaction mixture is poured into 300 ml of water, extracted with ethyl acetate, washed with water, brine, dried over MgSO4, and evaporated. The crude beige product is recrystallized from 130 ml of ethanol, yielding 5.44 g (61%) of 4-{4-[4-(3-cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile as light beige crystals, melting point 128-130° C.

후처리

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude beige product is recrystallized from 130 ml of ethanol

출처 및 근거

ORD 기록
ord-7395024a17624351a2345a5625fb037c
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703182B1

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