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

HRID 2387886노트

반응식

HRID 2387886 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-417309f09bfe44d385ebdea262e8db55
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268990B2

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