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

HRID 560053

反応式

HRID 560053 の反応式
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.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=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.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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0835510b88e74f8f87f08ae99a818abd
出典データセット
uspto-grants-2011_11
特許番号
US08063087B2

関連ノート

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