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

HRID 1617241노트

반응식

HRID 1617241 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab4b018e123840dfbb8c355585409967
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765939B2

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