Potassium Carbonate → 3-Ethoxy-2-(4-fluoro-phenyl)-cyclopent-2-enone

HRID 9274

反応式

HRID 9274 の反応式
Br[C:2]1[C:3](=[O:10])[CH2:4][CH2:5][C:6]=1[O:7][CH2:8][CH3:9].C([O-])([O-])=O.[K+].[K+].[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.C1C=CC=CC=1.O.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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:8]([O:7][C:6]1[CH2:5][CH2:4][C:3](=[O:10])[C:2]=1[C:21]1[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=1)[CH3:9]

参加物

12

反応物 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 107269112-Bromo-3-ethoxycyclopent-2-enone

生成物 1

HCID 219861393-Ethoxy-2-(4-fluoro-phenyl)-cyclopent-2-enone収率 70%

試薬・触媒・溶媒 8

HCID 11776Triphenylphosphine触媒HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 178418789HCID 178418789、化合物触媒HCID 241Benzene溶媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

2-Bromo-3-ethoxy-cyclopent-2-enone (Intermediate NINE2) (10.5 g, 51.2 mmol) and K2CO3 (14.2 g, 102 mmol) in toluene (100 mL), benzene (100 mL) and H2O (50 mL) was treated with a solution of 4-fluorophenylboronic acid (9.31 g, 66.5) in EtOH (100 mL). Tetrakis(triphenylphosphine)palladium(0) Pd(PPh3)4 (3 g, 2.6 mmol), bis(dibenzylideneacetone)palladium(0), Pd2(dba)3 (0.47 g, 0.5 mmol) and triphenylphosphine (0.27 g, 1.0 mmol) were added and the mixture was purged with N2 for 15 m. The mixture was heated to 100° 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 2.5% EtOAc:CH2Cl2 to give 3-ethoxy-2-(4-fluoro-phenyl)-cyclopent-2-enone (Intermediate NINE3) 7.85 g (70%).

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 2.5% EtOAc

出典と根拠

ORDレコード
ord-1b99ecc263fc43ae8cb7d0f030d361c9
出典データセット
uspto-grants-2006_08
特許番号
US07091232B2

関連ノート

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