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

HRID 48136

Reaction equation

HRID 48136 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7395024a17624351a2345a5625fb037c
Source dataset
uspto-grants-2004_03
Patent number
US06703182B1

Linked notes

Loading…