Benzeneacetonitrile, 4-bromo- → Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

HRID 2387886ノート

反応式

HRID 2387886 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:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=1.C([O-])(O)=O.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.CCOCC>[C:18]([CH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:8][CH:3]([C:2](=[O:1])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])=[CH:12][CH:13]=1)#[N:19]

参加物

7

反応物 3

HCID 27914Benzeneacetonitrile, 4-bromo-HCID 516892Sodium BicarbonateHCID 5080248Methyl 3-hydroxy-2-methylen-butanoat

生成物 1

HCID 59590640Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A stirred mixture of methyl 3-hydroxy-2-methylenebutanoate (19.5 g), 2-(4-bromophenyl)acetonitrile (40 g), PdOAc2 (2 g), tetrabutylammonium bromide (40 g) and NaHCO3 (31.5 g) in THF (300 ml) was heated under N2 at reflux for 24 h. The mixture was cooled, diluted with ether (500 ml) and filtered through celite. The filtrate was washed with water, dried and evaporated under reduced pressure to give an oil, used crude in next step.

後処理

  1. temperaturewas heated under N2
  2. temperatureat reflux for 24 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. washThe filtrate was washed with water
  6. customdried
  7. customevaporated under reduced pressure
  8. customto give an oil

出典と根拠

ORDレコード
ord-417309f09bfe44d385ebdea262e8db55
出典データセット
uspto-grants-2012_09
特許番号
US08268990B2

反応ノート

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