Ethyl 4-iodobenzoate → HCID 11160945, compound

HRID 984519Notes

Reaction equation

HRID 984519 reaction equation
O([Si](C)(C)C)[K].[CH2:7]([O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)[CH3:8]>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]>[CH2:7]([O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14](/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:13][CH:12]=1)[CH3:8]

Participants

4

Reactant 2

HCID 142891Ethyl 4-iodobenzoateHCID 178504318HCID 178504318, compound

Product 1

HCID 11160945HCID 11160945, compound

Reagents, catalysts & solvents 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Procedure

Following General Procedure II, a mixture of KOSiMe3 (570 mg, 4.0 mmol, 2.0 equiv), (E)-21 (379 mg, 2.2 mmol, 1.1 equiv), ethyl-4-iodobenzoate (2.0 mmol) and Pd(dba)2 (58 mg, 0.1 mmol, 0.05 equiv) was stirred at room temperature for 15 min, and then was filtered through SiO2. Purification by column chromatography (SiO2, Hexane/Ethyl Acetate, 50/1) and Kugelrohr distillation afforded 413 mg (84%) of (E)-154f as colorless oil.

Workup

  1. filtrationwas filtered through SiO2
  2. customPurification
  3. distillationby column chromatography (SiO2, Hexane/Ethyl Acetate, 50/1) and Kugelrohr distillation
  4. customafforded 413 mg (84%) of (E)-154f as colorless oil

Sources & evidence

ORD record
ord-dc77b31795d84646beff5da841acbfd7
Source dataset
uspto-grants-2005_03
Patent number
US06867323B2

Reaction notes

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