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

HRID 48136

反応式

HRID 48136 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 702Ethanol溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7395024a17624351a2345a5625fb037c
出典データセット
uspto-grants-2004_03
特許番号
US06703182B1

関連ノート

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