Potassium Carbonate → 4-(2-Methyl-5-oxo-1-cyclopenten-1-yl)benzonitrile

HRID 28735

반응식

HRID 28735 반응식
Br[C:2]1[C:3](=[O:8])[CH2:4][CH2:5][C:6]=1[CH3:7].C([O-])([O-])=O.[K+].[K+].[C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)#[N:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:7][C:6]1[CH2:5][CH2:4][C:3](=[O:8])[C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([C:15]#[N:16])=[CH:18][CH:19]=1

참가 물질

10

반응물 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343264-Cyanophenylboronic acidHCID 44370092-Bromo-3-methyl-2-cyclopenten-1-one

생성물 1

HCID 219861594-(2-Methyl-5-oxo-1-cyclopenten-1-yl)benzonitrile

시약·촉매·용매 5

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 178418789HCID 178418789, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

2-Bromo-3-methyl-cyclopent-2-enone (Intermediate TEN1) (commercially available from Aldrich) (2.04 g, 11.4 mmol) and K2CO3 (3.16 g in 11 mL H2O) in toluene (45 mL) was treated with a solution 4-cyanophenylboronic acid (commercially available from Aldrich) (2.2 g, 15 mmol) in EtOH (27 mL). Tetrakis(triphenylphosphine)palladium(0) Pd(PPh3)4 (0.4 g), bis(dibenzylideneacetone)palladium(0), Pd2(dba)3 (0.055 g, ˜5 mol %) and triphenylphosphine (0.4 g) were added and the mixture was purged with N2 for 15 m. The mixture was heated to 80° C. for 15 h. The mixture was diluted with water and EtOAc:hexane. After extracting with EtOAc:hexane, the combined organic layers were dried over MgSO4, filtered and evaporated to dryness. The crude oil was purified by column chromatography on silica gel with CH2Cl2 to give 4-(2-methyl-5-oxo-cyclopent-1-enyl)-benzonitrile (Intermediate TEN2) 1.74 g.

후처리

  1. customthe mixture was purged with N2 for 15 m
  2. additionThe mixture was diluted with water and EtOAc
  3. extractionAfter extracting with EtOAc
  4. dry with materialhexane, the combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude oil was purified by column chromatography on silica gel with CH2Cl2

출처 및 근거

ORD 기록
ord-f0b33d8607b84a368aef09dc29bf8f36
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419994B2

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