Water → HCID 12856969, compound

HRID 1929524Notes

Reaction equation

HRID 1929524 reaction equation
I[C:2]1[C:3](=[O:7])[CH2:4][CH2:5][CH:6]=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.O1CCCC1.O>[Cl-].[NH4+].[Ag-]=O.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[C:3](=[O:7])[CH2:4][CH2:5][CH:6]=2)=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 742994-Chlorophenylboronic acidHCID 108674992-Iodo-cyclopent-2-enone

Product 1

HCID 12856969HCID 12856969, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 11773TriphenylarsineCatalystHCID 178418778HCID 178418778, compoundCatalystHCID 25517Ammonium ChlorideSolvent

Procedure

4.8 g 2-Iodo-cyclopent-2-enone (prepared as described in Org. Lett. 6, 2004, page 3289), 5.4 g 4-chlorophenylboronic acid, 8.5 g silver(I)oxide, 0.425 g triphenylarsine and 0.265 g Pd(C6H5CN)2Cl2 were added to 90 ml tetrahydrofurane and 20 ml water. The reaction mixture was stirred under nitrogen atmosphere for 16 hours. The reaction mixture was diluted with ammonium chloride, filtered and extracted twice with ethyl acetate. The residue was purified by chromatography and the solvent was evaporated. 3.44 g 2-(4′chlorophenyl)cyclopent-2-enone were obtained (m.p. 71-72° C.).

Workup

  1. filtrationfiltered
  2. extractionextracted twice with ethyl acetate
  3. customThe residue was purified by chromatography
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-875d8a681c804cf2924a263b1632f57b
Source dataset
uspto-grants-2012_05
Patent number
US08188088B2

Reaction notes

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