반응 #9371

반응 방정식

2-Bromo-3-methyl-cyclopent-2-enone

K2CO3

4-cyanophenylboronic acid

triphenylphosphine

→

4-(2-methyl-5-oxo-cyclopent-1-enyl)-benzonitrile

용매

toluene

EtOH

반응 조건

후처리

1. 1
   기타the mixture was purged with N2 for 15 m
2. 2
   workup.ADDITIONThe mixture was diluted with water and EtOAc
3. 3
   추출After extracting with EtOAc
4. 4
   건조hexane, the combined organic layers were dried over MgSO4
5. 5
   여과filtered
6. 6
   기타evaporated to dryness
7. 7
   기타The crude oil was purified by column chromatography on silica gel with CH2Cl2

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.

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