(3-Bromophenyl)acetonitrile → Methyl 2-(3-(cyanomethyl)benzyl)-3-oxobutanoate

HRID 1617241ノート

反応式

HRID 1617241 の反応式
[OH:1][CH:2]([CH3:9])[C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].Br[C:11]1[CH:12]=[C:13]([CH2:17][C:18]#[N:19])[CH:14]=[CH:15][CH:16]=1.C([O-])(O)=O.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[C:18]([CH2:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:8][CH:3]([C:2](=[O:1])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])#[N:19]

参加物

6

反応物 3

HCID 36023(3-Bromophenyl)acetonitrileHCID 516892Sodium BicarbonateHCID 5080248Methyl 3-hydroxy-2-methylen-butanoat

生成物 1

HCID 68414943Methyl 2-(3-(cyanomethyl)benzyl)-3-oxobutanoate

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A stirred mixture of methyl 3-hydroxy-2-methylenebutanoate (11.37 ml), 2-(3-bromophenyl)acetonitrile (22 g) PdOAc2 (3.15 g), tetrabutylammonium bromide (30.1 g) and NaHCO3 (19.64 g) in THF (40 ml) was heated at reflux for 24 h. The mixture was partitioned between ether and water, the organics separated, washed with water, dried and evaporated under reduced pressure to give the subtitle compound, 22 g.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. customThe mixture was partitioned between ether and water
  4. washthe organics separated, washed with water
  5. customdried
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-ab4b018e123840dfbb8c355585409967
出典データセット
uspto-grants-2014_07
特許番号
US08765939B2

反応ノート

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